Here is how the last 10 playoff runs went for the Toronto Maple Leafs (spoiler alert: they were all hot garbage), starting, perhaps, with the ugliest one of all. The Leafs would lose that game 5-4 in overtime, which still haunts many fans well over a decade after the fact. The Leafs once again fell to the Bruins in seven games in a back-and-forth series in the 2019 Playoffs. 2021: Montreal CanadiensThe 2021 playoffs were touted as the Leafs' year, and they even had that "All or Nothing" documentary made. The Leafs held a 2-0 series lead going into Game 3 of their second-round series after taking out the Ottawa Senators in 6 games during Round 1.