Few franchises in the NHL are more tortured than that of the Toronto Maple Leafs. One of the Original Six, the franchise's struggles have been well-documented, with no Stanley Cups (or even Cup Final appearances) since 1967.
And in recent years the struggle has been especially rough, as the team has made the postseason five straight years... and has seen five early exits in excruciating fashion, with multiple "win-and-advance" attempts going for naught. So if you're a Bruins fan delighting in a rival's misery or a masochist Toronto die-hard, here are the ways in which the Leafs haven't advanced in recent times:
2013: We begin our journey eight years ago, as the Leafs made their first postseason since before the lockout. Against the rival Bruins it looked like a potential quick first-round exit, down 3-1 in the series, but that wouldn't have shattered the heart as cruelly. Instead, Toronto eeked out a pair of 2-1 victories to force a decisive Game 7 -- when things really took a turn.
Toronto led 4-1 with less than 12 minutes to go in regulation... and you probably remember the rest. Nathan Horton made it 4-2 at the 9:18 mark. Then with the goalie pulled Milan Lucic and Patrice Bergeron scored twice in 31 seconds to tie it and force overtime. From there it seemed all but a formality when Bergeron's second of the game capped one of the more improbable Game 7 comebacks in NHL history.
Win-once-and-advance record: 0-1
2017: This first-round exit is the only one that doesn't feature the Leafs needing just a single win to advance... but that doesn't make it any less heartbreaking. In the six-game loss to the Capitals, five of the games went to overtime. Toronto won two of the first three before Washington tied the series with the only regulation victory in Game 4.
Then Games 5 and 6 both went to OT, and both ended the same way: with 2-1 Washington victories on game-winners from Justin Williams and Marcus Johannson to advance.
Win-once-and-advance record: 0-0 (aggregate since 2013: 0-1)
2018: In a similar fashion as 2013, Toronto found itself trailing its first-round series to Boston 3-1, and again the Leafs would win Games 5 and 6 to take the series back to Beantown for a winner-moves-on Game 7. Though there wasn't a magical comeback by the B's, there was another third period meltdown by Toronto. A pair of second period goals by the Leafs gave them a 4-3 lead, and then the Bruins came out and steamrolled Toronto in the final 20 minutes, using a 4-0 period to win by a 7-4 final.
Win-once-and-advance record: 0-1 (aggregate since 2013: 0-2)
2019: A 2-1 win in Game 5 put the Leafs up 3-2 in the series against the rival Bruins with a return to home ice on the docket. In Game 6 Boston outshot Toronto 41-24 and won 4-2 to force Game 7, where the Bruins got a pair of late first period goals to take control. The Leafs trailed 3-1 late before Boston notched a pair of empty netters to inflate the score to a 5-1 final.
Win-once-and-advance record: 0-2 (aggregate since 2013: 0-4)
2020: With the COVID-shortened season, the league used a qualifying round for most of the league to make the official "Stanley Cup Playoffs". In a best-of-five with Columbus, Toronto forced a do-or-die fifth game after winning Game 4 in overtime. Yet despite outshooting the Jackets 33-22, Columbus scored early in the first period and never looked back in a comfortable 3-0 win to advance.
Win-once-and-advance record: 0-1 (aggregate since 2013: 0-5)
2021: Up 3-1 in the series against Montreal, the top seed in the North was a goal away from ending things on two different occasions. In Game 5 after falling behind 3-0 Toronto rebounded to force overtime, only to watch Nick Suzuki beat them 59 seconds into the extra session. No worries, though. In Game 6 they used two goals in the final ten minutes of regulation to again force OT... but lost again 3-2. Two overtime losses set up a largely predictable Game 7, in which Montreal controlled things throughout in a 3-1 victory to send the top-seed home packing.
Win-once-and-advance record: 0-3 (aggregate since 2013: 0-8)