- Dave Keon won his first Stanley Cup with the Maple Leafs in his second NHL season.
- Six of the 11 best Leafs players won at least four Stanley Cups with the franchise.
- Mats Sundin has the most points (987) and goals (420) in franchise history.
One of the original six NHL teams, the Toronto Maple Leafs are a storied franchise with history and success stories.
The franchise has won the Stanley Cup 13 times and has seen some of the NHL’s best players go through their ranks.
While online sports betting has only recently become mainstream, many of those championship teams would have had the best Stanley Cup odds entering the season.
Here are the Maple Leafs’ 11 best players of all time, three of whom won four Stanley Cups with the franchise.
11 Best Maple Leafs Players in Team History
| Rank | Player | Position | Maple Leafs Years |
| 1 | Dave Keon | Centre | 1960-75 |
| 2 | Frank Mahovlich | Left Winger | 1956-68 |
| 3 | Mats Sundin | Centre | 1994-08 |
| 4 | Darryl Sittler | Centre | 1970-82 |
| 5 | Auston Matthews | Centre | 2016-25 |
| 6 | Johnny Bower | Goaltender | 1958-70 |
| 7 | Borje Salming | Defence | 1973-89 |
| 8 | George Armstrong | Right Winger | 1949-71 |
| 9 | Tim Horton | Defence | 1949-70 |
| 10 | Syl Apps | Centre | 1936-48 |
| 11 | Ted Kennedy | Centre | 1942-57 |
Greatest Maple Leafs of All Time
1. Dave Keon
Dave Keon found success almost immediately after entering the NHL, winning his first Stanley Cup with the Maple Leafs in his second season.
Keon also led the Maple Leafs to glory in the subsequent two seasons, guiding the franchise to its second and last three-peat.
He was just 22 years old when he led Toronto to its 1961-62 Stanley Cup triumph. Keon won four Cups in 15 seasons with the Maple Leafs.
He wasn’t too shabby offensively either, scoring 858 points (365 goals and 493 assists) in 1,062 games.
2. Frank Mahovlich
Frank Mahovlich is a household name recognized instantly by most hockey aficionados. He donned the Maple Leaf between 1956-68 and, like Keon, won four Stanley Cups in Toronto.
The left winger took no prisoners and endeared himself to fans for the hard-nosed way he went about his business. Mahovlich went on to play for two more teams, the Detroit Red Wings and Montreal Canadiens, before hanging up his skates in 1974.
3. Mats Sundin
Mats Sundin is part of the more recent generation of Maple Leafs greats. He has the most points (987) and goals (420) all time and averaged a point per game in his 13 seasons in Toronto.
The one knock on Sundin is his lack of playoff success. During his time in Toronto (1994-2008), the Maple Leafs made the conference final twice (1999 and 2002), losing both.
4. Darryl Sittler
Like Sundin, Darryl Sittler never won a Cup with the Maple Leafs. However, Sittler will forever be recognized as one of the Maple Leafs’ greatest.
He scored 916 points (389 goals and 527 assists) in 844 games across 12 seasons in Toronto. Sittler has the second-most points and goals and tallied 1.09 points per game, one of the best scoring rates of any Maple Leaf.
He led the team to the conference final in 1978, which they lost to the Canadiens.
5. Auston Matthews
Auston Matthews is a generational talent who has accomplished incredible personal feats during his eight-plus seasons in Toronto. He’s won three Rocket Richard Trophies and should be among the hockey odds contenders to add to that total for years to come.
Matthews won the Calder Trophy in 2016-17 and the Hart Trophy and Ted Lindsay Award in 2021-22. He’s scored 649 points in 563 games during his first eight seasons, the most points per game (1.15) of any Maple Leaf.
6. Johnny Bower
Johnny Bower played his first game with the Maple Leafs when he was 33. He certainly made up for lost time, becoming one of five Maple Leafs netminder to win the Vezina Trophy. He finished his career with two Vezina Trophies while winning four Stanley Cups in Toronto.
7. Börje Salming
Börje Salming is the Maple Leafs’ top-scoring defenceman of all time, notching 768 points (148 goals and 620 assists) in 1,099 games. He’s also just behind the legendary Tim Horton in penalty minutes, accumulating 1,292 minutes.
8. George Armstrong
As part of the one-team man collection, George Armstrong played at least a game for the Maple Leafs in 21 seasons. He was a Maple Leafs’ lifer, endearing himself to locals. Armstrong has the fifth-most points in franchise history, finishing with 713 in 1,188 games. Those 1,188 games are the most by any Leaf.
Armstrong won four Cups with Toronto and was the captain in each, a Maple Leafs record. It’s only fitting that he has secured a spot among the 11 Toronto greats.
9. Tim Horton
Horton stimulated Torontarians more than the coffee named after him ever will. The bruising, powerful, no-nonsense defenceman played at least one game for the Maple Leafs in 20 of his 24-season career. He won four Stanley Cups and secured a spot on six postseason All-Star teams
Horton was also known for his residence in the sin bin, where he spent 1,389 minutes, the fourth-most by a Maple Leaf.
10. Syl Apps
Like Armstrong, Syl Apps devoted his entire career to the Maple Leafs. While he only played for 10 seasons and retired at the ripe age of 33, Apps was the first Maple Leaf to win the Calder Trophy. He won three Stanley Cups and the Lady Byng Memorial Trophy.
In addition, Apps was a point-per-game player, notching 432 in 423 games.
11. Ted Kennedy
Ted Kennedy won a handful of Stanley Cups with Toronto and, like Apps and Armstrong, was a one-team man, playing at least a game in 14 seasons as a Maple Leaf. He finished his career with 560 points (230 goals and 330 assists) in 696 games.
He is among three players to win the Hart Trophy with the Maple Leafs. Kennedy won the Hart Trophy in 1954-55, following Babe Pratt, who took the honour in 1943-44. Matthews joined them when he was anointed as the MVP in 2021-22.