A Celebration of Canadian Futility

Canadian hockey fans probably don’t want to talk about it.

“It,” of course, is the nation’s Stanley Cup drought. With the elimination of the Montreal Canadiens, the country is now assured of going Cupless for the 20th consecutive season. During that span, we’ve seen Canadian teams fall one win short some years and not even come close in others. It’s all been very painful.

But just how painful? Oh, we’re going to talk about it, Canada. We’re going to talk about it in detail. Specifically, we’re going to look back at each of those seasons, and we’re going to rank them based on just how much it hurt. It’s the only way we can begin to heal.

So here’s the deal — for each of the country’s 20 consecutive Cupless seasons, we’re going to take the last surviving Canadian team (based on playoff games won) and rank the pain it caused based on three key categories:

Bandwagon factor: How much fun was the run? Was it a team that fans of other franchises could get behind, at least temporarily? Remember, any decent Canadian hockey fan’s default position is to root against the country’s other teams. But if the right story comes along, we can allow ourselves to get on board for a few weeks.

Hope index: How close did the team come? The length of the playoff run obviously factors heavily here, but the quality of the team does too. There are some teams that win a round or two without ever looking like a real threat to win it all, while others can bow out early but still have felt like they were this close.

Eventual heartbreak: Pretty self-explanatory — how badly did it all end? The previous two categories factor in here, too, since it always hurts more when you get suckered in by a fun team that looked like it really had a shot. We’ll award bonus points for losing in an especially painful and/or creative way.

We’ll take those three categories, then use them to come up with an overall rating (not an average), which will be the basis of our rankings. All of which will allow us to answer the question: In 20 years of Cupless Canadian misery, which years were the worst of them all?

It’s for the best, Canada. But it may hurt.

No. 20 — 1995

Last team standing: The Vancouver Canucks, who were swept by the Blackhawks in the second round.

Bandwagon factor: 3/10. This was a weird year. The first lockout had wiped out half the season, and even when play resumed it just never felt quite right. But the Canucks were likable enough, even though they’d already had a long run the year before.

Hope index: 5/10. Canada had won eight of the last 11 titles, and the Canucks had fallen just one game short the year before. We pretty much owned the Cup at this point.

Eventual heartbreak: 1/10. Ah, well, can’t win ’em all, right?

Overall misery rating: 2.3/10. Remember, we had no idea what was coming. We just assumed this was a temporary blip.

No. 19 — 2012

Last team standing: The Ottawa Senators, who lasted seven whole games before losing to the Rangers in the first round.

Bandwagon factor: 1/10. You saw the part about it being the first round, right? The Canucks were the only other Canadian team to even make the playoff this year, and they were the ones we expected to go deep. Once they were out, it took everyone a few days to remember Ottawa was still alive.

Hope index: 1/10. First … round …

Eventual heartbreak: 5/10. Any seven-game loss is tough, and this one saw the Senators blow a 3-2 series lead by dropping a pair of one-goal games.

Overall misery rating: 2.5/10. Shrug. After what was then 18 consecutive Cupless seasons, this one barely registered.

No. 18 — 1996

Last teams standing: A four-way tie, with the Leafs, Canadiens, Canucks, and Jets all lasting six games in the first round.

Bandwagon factor: 1/10. With four teams all going out within 24 hours (and a fifth, the Flames, eliminated a few games earlier), nobody had any time for bandwagons.

Hope index: 2/10. There were five Canadian teams in the playoffs. Somebody had to last for a round or two, right?

Eventual heartbreak: 5/10. Actually, this one needs an asterisk, because the Jets loss also spelled the end of NHL hockey in Winnipeg for 15 years. The franchise was known to be moving south once its season ended, so the elimination hurt. The others, not so much.

Overall misery rating: 2.6/10. Pretty much all of which is due to the Jets.

No. 17 — 1998

Last teams standing: The Edmonton Oilers and Ottawa Senators, both of whom lasted five games into the second round.

Bandwagon factor: 6/10. Both teams had pulled off first-round upsets, and the Senators had won a playoff round for the first time in their history. If you were into underdogs, you could get behind these teams.

Hope index: 2/10. They were nice stories, but nobody realistically thought either of these teams was winning the Cup.

Eventual heartbreak: 2/10. Both got thoroughly stomped in the second round.

Overall misery rating: 2.9/10. Four years and counting. The drought was officially on.

No. 16 — 2001

Last team standing: The Toronto Maple Leafs, eliminated by the Devils in Round 2.

Bandwagon factor: 3/10. This was right in the middle of the Mats Sundin era, and was one of four consecutive years that the Leafs were the last Canadian team standing. Many of those teams were reasonably likable. This one was not. In fact, by this point everyone other than die-hard Leafs fans hated this team. I can’t imagine why. They seemed like such a pleasant bunch.

Hope index: 3/10. The Leafs took a step back this season and were just a 90-point team. And by now, the pre-cap league had firmly settled into the Wings/Avs/Devils era of dominance; if you weren’t one of those three teams, you were a long shot.

Eventual heartbreak: 4/10. While everyone likes to pretend the Leafs immediately fell apart after the Tie Domi elbow, they actually took the Devils to Game 7. But their season ended with a 5-1 blowout loss, making it pretty clear this team just wasn’t good enough.

Overall misery rating: 3.2/10. This was definitely the least painful of the (surprisingly frequent) solo Leaf appearances on our list.

No. 15 — 2008

Last team standing: The Montreal Canadiens, eliminated by the Flyers in the second round.

Bandwagon factor: 6/10. Weirdly, this was the first time the Canadiens had been all alone as the country’s last team standing since their 1993 Cup run. They were a reasonably likable bunch, featuring Saku Koivu as captain and a rookie goalie named Carey Price.

Hope index: 5/10. This was a good team that went into the postseason as the East’s top seed. But they didn’t get far, dropping a second-round series to Philadelphia in five games.

Eventual heartbreak: 2/10. After a Habs’ overtime win in Game 1, the Flyers won four straight to take the series.

Overall misery rating: 4.0/10. After three straight Cup final appearances by Canadian teams, the Habs’ elimination left a confused country wondering why it was over so quickly.

No. 14 — 2013

Last team standing: The Senators, who dropped a second-round series to the Penguins.

Bandwagon factor: 5/10. Ottawa had gone through an astounding stretch of injuries to top players, then battled back to earn one of the final playoff spots. Then they smoked the Habs in five games, which will always earn you a few points in Canada.

Hope index: 2/10. They were a 7-seed, and they were facing a Penguins team we all thought was the definitive Cup favorite.

Eventual heartbreak: 4/10. As expected, they got smoked by Pittsburgh in five. The combined score of the last two games was 13-5.

Overall misery rating: 4.3/10. I’m awarding them a few bonus points for having to endure the sight of their beloved captain basically quitting on them.

No. 13 — 2000

Last team standing: The Maple Leafs, who lost to the Devils in the second round.

Bandwagon factor: 5/10. Nobody in Canada ever really wants to jump on the Leafs bandwagon, but this team was semi-likable and had the whole “Wendel’s last hurrah” thing going for it.

Hope index: 4/10. They were a 100-point team and had been to the conference finals the previous year, so they had a shot. But they weren’t one of the league’s elite teams, and it quickly became clear the Devils were just better.

Eventual heartbreak: 5/10. Their run ended with a whimper in a Game 6 loss in which they were credited with just six shots, presumably because New Jersey’s official scorer fell asleep halfway through the first period.

Overall misery rating: 4.4/10. This was right about the time when Canadian fans were starting to seriously freak out about the whole drought thing.

No. 12 — 2009

Last team standing: The Canucks, knocked out in Round 2 by the Blackhawks.

Bandwagon factor: 5/10. This was a fun team, with Roberto Luongo and the Sedin twins. They also had Sundin, which was divisive among the country’s many Maple Leafs fans — some were rooting for him to finally win his first Cup, while others hadn’t forgiven him for jumping ship.

Hope index: 6/10. It was a good team that marked the start of the Canucks’ stretch of five consecutive division titles. They swept the Blues in the opening round and looked like they had a shot until they ran into a tough second-round matchup.

Eventual heartbreak: 4/10. In what would be the beginning of a great rivalry, the Canucks met the Blackhawks in the second round. Vancouver jumped out to a 2-1 series lead before dropping three straight, including a wacky 7-5 loss to be eliminated.

Overall misery rating: 4.9/10. Welcome back to the party, Vancouver — this was its first time serving as Canada’s last team in 14 years.

No. 11 — 2010

Last team standing: The Canadiens, who lost to the Flyers in the conference finals.

Bandwagon factor: 6/10. This was the Jaroslav Halak year, when the Habs upset the Capitals and Penguins on their way to the third round. It wasn’t a great team — Scott Gomez was their second-leading scorer — but they had their charm. And they even had a cool song.

Hope index: 6/10. They were the East’s no. 8 seed, and nobody gave them a chance against the Caps, who’d won the Presidents’ Trophy with 121 points. But they pulled off the upset in seven games, and then did the same to the favored Penguins, at which point everyone started muttering about ghosts and destiny.

Eventual heartbreak: 5/10. After beating a pair of 100-plus-point teams to get to the conference finals, the Habs somehow wound up facing the 88-point Flyers. But they dropped the first two games of the series by a combined score of 9-0, and bowed out meekly in five.

Overall misery rating: 5.2/10. It was hard to feel like they ever really had a shot, but it was a fun ride while it lasted.

No. 10 — 1997

Last team standing: The Oilers, who lost in the second round to the Avalanche.

Bandwagon factor: 9/10. The Oilers had missed the playoffs for four consecutive years, officially burying any remnants of their dynasty days. Even worse, the league’s shifting economics had them stumbling dangerously close to “de facto farm team for the league’s rich teams” status. But they snuck into the postseason with just 81 points, then pulled off a memorable first-round upset over the Stars that featured this legendary Curtis Joseph robbery and Todd Marchant’s breakaway winner. From that point, everyone was on board.

Hope index: 2/10. Like I said, they had 81 points. The Stars upset was fun, but they still had the Avalanche and Wings in their way.

Eventual heartbreak: 3/10. The end came relatively painlessly, as the Avs beat them in five games.

Overall misery rating: 5.3/10. Fun fact: This marked the first time Canada had gone three consecutive years without a Cup since the Islanders’ dynasty, and the first time since 1940 that three different U.S. teams had won it in consecutive years.

No. 9 — 1999

Last team standing: The Maple Leafs, eliminated in the conference finals by the Sabres.

Bandwagon factor: 7/10. Toronto had missed the playoffs for two years straight, hadn’t won a round since 1994, and wasn’t expected to be any good. But Pat Quinn showed up, and suddenly the Leafs were all kinds of fun to watch, leading the league in scoring while leaving new goalie Curtis Joseph to fend for himself in the defensive zone. Also, Danny Markov.

Hope index: 7/10. With a few better teams getting knocked out early, the Leafs started to build up some decent “Why not us?” momentum. Their conference finals matchup with the Sabres was one they absolutely could have won, and that was especially true once Dominik Hasek was a surprise scratch in the first two games.

Eventual heartbreak: 4/10. They only managed to split the Hasek-less games, and once he came back the Sabres rolled over them to win in five.

Overall misery rating: 5.5/10. This was the deepest a Canadian team had gone since 1994.

No. 8 — 2014

Last team standing: The Canadiens, who lost to the Rangers in the conference finals.

Bandwagon factor: 8/10. Plenty of Canadian fans would never get behind the Habs no matter what, but this team was a lot of fun. You had the P.K. Subban factor, Carey Price, and a whole bunch of small guys running around. They shocked the Bruins, who were an easy team to root against. And for a while they had a great “nobody believes in us” vibe going, right until they played the card one too many times and everyone got sick of it.

Hope index: 7/10. Once they got past the Bruins, they looked like they had a great chance against the Rangers. They would have been a long shot to beat whoever came out of the West, but even that wasn’t out of the question with the way Price was standing on his head.

Eventual heartbreak: 7/10. Oh, right, Carey Price. He kind of has to stay healthy for all of this to work. Oops.

Overall misery rating: 7.3/10. There’s always next year. At least, that’s what Milan Lucic told me.

No. 7 — 2007

Last team standing: The Senators, who lost to the Ducks in five games in the Cup final.

Bandwagon factor: 5/10. Here’s a little secret: Nobody outside of Ottawa cares about the Senators. Still, they were a Canadian team in the Cup final, so a lot of fans went along with it … right up until Daniel Alfredsson started shooting pucks at people.

Hope index: 9/10. The Senators had been a good team for a long time, and this was right in the prime of the Alfredsson-Spezza-Heatley “pizza line” years. The goaltending was iffy, but they’d put up a 105-point season and then rolled through the Eastern Conference in just 15 games, so it wasn’t hard at all to picture them winning the Cup.

Eventual heartbreak: 7/10. Pro: They got crushed by the Ducks in five games, so they never really had time to get their hopes up. Con: They somehow managed to score the Stanley Cup–winning goal into their own net.

Overall misery rating: 7.6/10. This feels like it should be higher, doesn’t it? Maybe it was Cup final fatigue — this was the third consecutive year a Canadian team made it this far and lost — but I don’t remember this feeling like that big of a deal.

No. 6 — 2002

Last team standing: The Maple Leafs, knocked out in the conference finals by the Hurricanes.

Bandwagon factor: 7/10. Even though this was essentially the same Leafs team that everyone hated in 2001, they earned some solid underdog karma when an early injury took Sundin out of the lineup. That should have been it for the Leafs, but they won a pair of seven-game series to advance to the conference finals for the fourth time in a decade. They were still occasionally unlikable — Shayne Corson got suspended for trying to kick a guy in the head during a fight — but you could definitely get behind them.

Hope index: 7/10. By the time the conference finals rolled around, Sundin was ready to return and the Leafs had drawn a mediocre Hurricanes team they absolutely should have beaten. The powerhouse Red Wings were waiting, but a trip to the Cup final seemed like a sure thing.

Eventual heartbreak: 8/10. Facing elimination on home ice and trailing 1-0 late in Game 6, the Leafs tied the game in the dying seconds on a memorable Sundin goal that led to Joe Bowen’s classic “Don’t tell me about heart and dedication” call. Then Martin Gelinas scored in overtime and it was over.

Overall misery rating: 7.7/10. This one still stings. Arturs Irbe? Get bent, hockey gods.

No. 5 — 2003

Last team standing: The Senators, who lost to the Devils in seven in the conference finals.

Bandwagon factor: 6/10. The Senators were past their “scrappy underdog” phase by now and well into their “Jacques Martin strangles the life out of the game” years. They were really good, though, winning the Presidents’ Trophy.

Hope index: 9/10. By this point everyone just assumed they’d eventually lose to the Maple Leafs. But when Toronto went out early, the field suddenly opened up, and by the time they hosted the Devils in Game 7 of the conference finals, the just-happy-to-be-there Mighty Ducks were waiting in the final. It’s not an exaggeration to say that the deciding game of this series felt like it was for the Stanley Cup.

Eventual heartbreak: 8/10. Despite being favored to beat the Devils, the Sens fell behind 3-1 before winning at home to force a Game 6, which they won on a Chris Phillips overtime goal. Then, with two minutes left in a tied Game 7 at home, this happened.

Overall misery rating: 7.8/10. This hurt at the time. Watching the Devils roll take down the Mighty Ducks in seven games to win the Cup made it a whole lot worse.

No. 4 — 2011

Last team standing: The Canucks, who lost to the Bruins in Game 7 of the Cup final.

Bandwagon factor: 2/10. There’s no nice way to say this: The 2011 Canucks were one of the most hateable teams in recent NHL history. They dove, they whined, they taunted, they bit. Put it this way — they turned the Boston Bruins into a likable team by comparison. Canadian fans aren’t big bandwagon jumpers by nature, but I’ve never seen a team get so little love from the nation’s fans.

Hope index: 10/10. The Canucks were the Presidents’ Trophy winners, had the league MVP/Art Ross winner, the top setup man, and the best goaltending numbers. And after a tough opening series against the Hawks in which they nearly blew a 3-0 series lead, they’d been getting stronger as the playoffs went on. They faced the Bruins in the Cup final, a team they finished 14 points ahead of in the regular season. The Cup was theirs to win.

Eventual heartbreak: 9/10. After winning the first two games of the final, the Canucks collapsed in Boston, losing Games 3 and 4 by a combined score of 12-1. But they won Game 5 and had two chances to seal the deal, including a Game 7 at home. They were stomped in both games and had to watch the Bruins celebrate the Cup on their home ice. Then their fans rioted.

Overall misery rating: 8.6/10. Sure, most of us Canadians hated this version of the Canucks just as much as you Americans did. But to see a franchise get this close to its first Cup and then hit the wall the way Vancouver did was downright painful.

No. 3 — 1994

Last team standing: The Canucks, who lost in Game 7 of the Cup final to the Rangers.

Bandwagon factor: 9/10. This was basically the polar opposite of the 2011 team: Everyone liked them. They had Pavel Bure, who was probably the most exciting player in the league. Good Canadian boy Trevor Linden was the captain, Kirk McLean was in net, and the roster was filled out with a nice mix of nonthreatening role players and cranky old guys. And they’d only finished one game over .500, so they were a great underdog story.

Hope index: 6/10. The Canucks were long shots when the playoffs started, but quickly established themselves as a legitimate threat by beating the Flames on this incredible Bure double-overtime winner. By the time they arrived in the Cup final to face the heavily favored Rangers, they had a distinct “team of destiny” feel.

Eventual heartbreak: 10/10. The Canucks dropped three of the first four games in the final but rallied back valiantly to force Game 7, only to lose a heartbreaker when Nathan LaFayette hit the post. They were that close. Also, this photo made everyone sad.

Overall misery rating: 9.2/10. This one absolutely could have taken top spot on our list. The only thing holding it back is timing — there was no Cup drought to speak of in 1994, so we didn’t realize quite how painful this would all seem in hindsight.

No. 2 — 2006

Last team standing: The Oilers, who lost to the Hurricanes in the seventh game of the Cup final.

Bandwagon factor: 9/10. The Oilers made what seemed like one of the all-time greatest underdog runs in sports history, going all the way to the Cup final as a no. 8 seed. That included a shocking first-round upset of the Red Wings, who’d piled up 124 points during the season and were supposed to steamroll them. Mix in the fact that Edmonton hadn’t won a playoff round in eight years, and they were a feel-good story that nobody hesitated to get behind. We even all pretended to like Chris Pronger!

Hope index: 8/10. Nobody gave Edmonton a chance heading into the postseason. In hindsight, that was probably unfair — they’d been a very good team that had been derailed by awful goaltending, which they’d remedied by picking up Dwayne Roloson at the deadline. And once they started rolling, we all talked ourselves into them. Remember, this was the post-lockout year, with the debut of the salary cap and all sorts of new rules. It felt like a new world in which things like “Edmonton Oilers Cup run” seemed plausible.

Eventual heartbreak: 10/10. Facing a very winnable Cup final matchup against the Hurricanes, the Oilers watched in horror as Roloson was hurt late in Game 1, which led to backup Ty Conklin giving up this ridiculous game-winner. The Hurricanes led the series 2-0 and 3-1, but Edmonton clawed back to force a seventh game, in which it fell agonizingly short.

Overall misery rating: 9.6/10. I’m still not completely over this one. Honestly, you could tell me this should be no. 1 on the list and I wouldn’t argue much.

No. 1 — 2004

Last team standing: The Calgary Flames, who lost to the Lightning in Game 7 of the Cup final.

Bandwagon factor: 10/10. If you programmed a super-computer to generate the ultimate bandwagon team, it would spit out the 2004 Calgary Flames. They had 94 points, which was good enough for them to just barely be considered a quasi-contender, but bad enough that they were permanent underdogs. They hadn’t made the playoffs in eight years, so nobody hated them. They never had it easy, playing an NHL-record 26 playoff games. They had Jarome Iginla as captain, Darryl Sutter as coach, great fans, and a lovable European goalie nobody had ever heard of. And they were the first Canadian team to make it to the Cup final in 10 years.

Hope index: 8/10. This was one of the unlikeliest runs in playoff history, and they didn’t even get any lucky matchups along the way — all four teams they faced had 100-plus points. After a decade between Cup final appearances, Canadian hockey fans had been trained to expect the worst, so we may have been slow to warm up to the Flames. But once the bandwagon started rolling, it was jammed.

Eventual heartbreak: 10/10. With a 3-2 series lead in the final and a chance to win the Cup on home ice, the Flames scored what appeared to be the winning goal in the dying minutes of regulation. To this day, Flames fans swear it was in, but it didn’t count. The Lightning went on to win Game 6 in double overtime, then took Game 7 by a 2-1 margin.

Overall misery rating: 9.7. The Flames slip past their Alberta rivals to just barely take the top spot. What sort of misery do the hockey gods have in mind for us over the next two decades? The Canadian mind boggles.

Filed Under: NHL, Montreal Canadiens, Ottawa Senators, Toronto Maple Leafs, Vancouver Canucks, Winnipeg Jets

Sean McIndoe ’s work can be found at Down Goes Brown. When he's not writing, he makes hockey jokes on Twitter at @downgoesbrown.

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