It has finally happened. The Montreal Canadiens and the Toronto Maple Leafs will meet in the NHL playoffs for the first time in 42 years. Surprisingly for two teams that are over 100 years old. they have only met in the post-season 15 times. The Leafs have met two teams more times than the Canadiens - Boston Bruins with 16 series played (8-8 record) and the Detroit Red Wings with 23 series played (12-11 record).

It’s a close record, and it could be tied with this 16th series. Hopefully it is.

1918 NHL Championship - Toronto Arenas over the Canadiens 10-7 total goals

The Toronto Arenas first season gave them their first NHL title. The NHL championship was between the two teams who won the first and second half of the season. The NHL champions would then play the Pacific Coast Hockey Association champions for the Stanley Cup.

The Arenas came in second in the first 14 game half of the season, behind the Canadiens, and won the second half, though it was only eight games long after the Montreal Wanderers ceased operations in January 1918. The first asterisk season! Toronto would easily win game one by a score of 7-3 at home, and lose the game in Montreal 4-3, but take the total goal series. They would go on to defeat the Vancouver Millionaires three games to two and win the Stanley Cup.

1925 NHL Championship - Montreal Canadiens over the Toronto St. Patricks 5-2 total goals

Montreal and Toronto met for the second time in another playoff with an asterisk. The Hamilton Tigers were the first place team in the NHL this season, however the players went on strike and the Tigers would not play again in the NHL. So the championship was between second place Montreal and third place Toronto. Things wouldn’t go as well for Toronto, since the Canadiens had Georges Vezina in net for this series. Luckily the Canadiens would lose the Stanley Cup to the Victoria Cougars, three games to one.

1944 NHL Playoffs - Round 1 - Montreal Canadiens over the Toronto Maple Leafs 4-1

The two teams would wait almost 20 years for another playoff series, and the NHL had moved on to a best of seven playoff format by then. The Leafs and Habs would meet in round one this year, but after winning game one 3-1, the Leafs would lose four straight including an 11-0 rout in game five.

The Canadiens would sweep the Blackhawks in the finals.

1945 NHL Playoffs - Round 1 - Toronto Maple Leafs over the Montreal Canadiens 4-2

Back again the next season, we would see the Leafs take this series in one more game. The series was close with the Leafs taking a 3-1 lead after a 4-3 overtime win and it looked like the Canadiens were going to run away with the rest of the series in game five after they won 10-3 (A four goal performance by Maurice Richard helped). The Leafs would win a squeaker in game six, 3-2, and the series.

The Leafs would go on to win the Stanley Cup in seven games over the Detroit Red Wings. They went up 3-0 in the series before Detroit came back to force a game seven. Typical Leafs.

1947 Stanley Cup Finals - Toronto Maple Leafs over Montreal Canadiens 4-2

After missing the playoffs in 1946, the Leafs would come back to the championship round after defeating the Detroit Red Wings 4-1 in the semi-finals. The two teams traded shutouts in games one and two before the Leafs would take games three, four, and six.

1951 Stanley Cup Finals - Toronto Maple Leafs over Montreal Canadiens 4-1

A three year gap didn’t mean the Leafs weren’t winning - they took two of three Stanley Cups in this time and in 1951 they got their fourth cup in five years. There was a gap the size of the Pacific Ocean between Montreal and Toronto in the standings. Toronto had a 41-16-16 record and the Habs had a 25-30-15 record. The playoff format was 1 v 3 and 2 v 4, and the Canadiens upset the Red Wings 4-2 in round one to meet Toronto in the finals.

Even though the series was won 4-1 by Toronto every single game went to overtime, with the game winning goal famously scored by Bill Barilko.

1959 Stanley Cup Finals - Montreal Canadiens over Toronto Maple Leafs 4-1

The Maple Leafs went on a downturn after that cup win, making the playoffs in only four out of seven seasons and never winning a round. That would change in 1959 when the upstart 4th place Leafs took the Boston Bruins to seven games in their opening round, with Gerry Ehman scoring the winner with less than three minutes to go.

However, this Montreal Canadiens team was beating up on the league the entire season - they were the only team to have a positive goal differential with a +100. The only game that was really close in this series was game three, which the Leafs took in overtime.

1960 Stanley Cup Finals - Montreal Canadiens over Toronto Maple Leafs 4-0

Unfortunately, we’re in the time frame for one of those pesky Canadiens dynasties. The Leafs did better in the regular season, placing second to Montreal. The first round was tough against Detroit - games three and four both went to overtime with game three needed three extra periods - but the Leafs won in six. Then the Canadiens swept Toronto, holding the Leafs to just five goals all series.

1963 NHL Playoffs - Round 1 -  Toronto Maple Leafs over Montreal Canadiens 4-1

Coming off their 1962 Stanley Cup win, the Maple Leafs eeked out first overall, winning by just one point over the Chicago Blackhawks and two over the Montreal Canadiens. First and third met in round one and the games were kept close, within one or two goals, until game five when the Maple Leafs blew out the doors, winning 5-0 in what would be Jacques Plantes final game as a Canadien. The Leafs would go on to win the Cup in ive games over Detroit.

1964 NHL Playoffs - Round 1 - Toronto Maple Leafs over Montreal Canadiens 4-3

Another meet up between first and third but this time they swapped positions. This was a close back and forth series featuring two shutouts and multiple one goal games. Dave Keon was the hero of this series, scoring a hat trick in game seven for the win. The Leafs would beat the Red Wings in seven games for the Cup.

1965 NHL Playoffs - Round 1 - Montreal Canadiens over Toronto Maple Leafs 4-2

All good things come to an end. The Maple Leafs won three Stanley Cups in a row, but couldn’t beat the Habs for a third playoff in a row. Multiple overtimes and close games kept things interesting, but the Leafs couldn’t beat the Canadiens.

1966 NHL Playoffs - Round 1 - Montreal Canadiens over Toronto Maple Leafs 4-0

The Montreal Canadiens 60s dynasty was in full swing by this point as they finished 11 points and 7 wins ahead of the Maple Leafs. Only game one was close, with a 4-3 win for Montreal. After that it all opened up for the Canadiens with 2-0, 5-2, and 4-1 wins to finish the sweep.

1967 Stanley Cup Finals - Toronto Maple Leafs over Montreal Canadiens 4-2

You know, it’s weird that we never hear about this years cup very often. The Maple Leafs were a very old team at this point and no one had much faith in them, or so the story goes. The Leafs were a distant third to the Montreal Canadiens, 19 points back and nine wins behind. Despite the Canadiens having two 6-2 wins in this series, the Maple Leafs fought hard and would win out in six games, including Bob Pulford scoring the game winner in a 3-2 double overtime win in game three.

1978 NHL Playoff Semi-Finals - Montreal Canadiens over Toronto Maple Leafs 4-0

After expansion brought the NHL up to 17 teams, the Maple Leafs and Canadiens would need to wait eleven years to meet again in the playoffs, and it was not worth the wait. The Canadiens would win the Norris Division easily with 112 points while the Maple Leafs got third in the Adams with 92 points. Montreal got a bye to the second round while the Leafs had to face off against LA in a best of three series. The Leafs beat the Kings 2-0, and then the Islanders in seven, while the rested Kings beat the Red Wings in five to set up the semi-final showdown.

Then the Habs swept Toronto. Moving on.

1979 NHL Playoffs - Round 1 - Montreal Canadiens over Toronto Maple Leafs 4-0

Once again the Leafs had to play an extra round in the playoffs, beating the Atlanta Flames in two games to get the chance to beat the 115 point Montreal Canadiens in a seven game series.

Boy did that not happen. The home gams for Montreal were solid blow outs, 5-2 and 5-1. The Leafs tried to make it a series at Maple Leafs Gardens, but would lose game three in double overtime, and then get swept in game four after Larry Robinson scored four minutes into overtime.

Fifteen playoff series, three team names, and multiple Stanley Cups on the line. Now the Maple Leafs will begin their eighth first round series against the Montreal Canadiens, and look for their first playoff win over Montreal since May 2nd, 1967.

They’ll do it.