Maple Leafs in the 2025 Playoffs: How Many Stanley Cups Have the Leafs Won?

With the 2025 Stanley Cup playoffs in full swing, the city of Toronto has been fully invested in the advancement of the Toronto Maple Leafs, hoping for a victory again! They have thus far made it to the second round of playoffs with a 5-4 win over the Florida Penthers in Game 1. Many Torontonians and Leafs’ lovers are hoping they can extend their lead in the series with game 2 coming up on Wednesday, May 7. But since we cannot forecast the future, all we can do is see their triumph in the past when it comes to the almighty Stanley Cup. In this article, we will cover all things Stanley Cup and Maple Leafs related. Go Leafs, Go!

How many Stanley Cups do the Toronto Maple Leafs have?

The Toronto Maple Leafs have won thirteen Stanley Cup Championships in history, making them the team with second most Stanley Cups in history. However, their last Stanley Cup victory was in 1967. The Toronto Maple Leafs have been in the Stanley Cup finals 21 times in total and have seen a victory in more than half of those times. It has been 58 years since the Leafs took the Stanley Cup home which is why a possible win is the most anticipated hope for Leafs’ fans.

What team has the most Stanley Cups in history? 

The team with the most Stanley Cup wins in history is also a Canadian team, the Montreal Canadians. The Montreal Canadians have 23 Stanley Cup wins since the founding of the NFL. The last time the Montreal Canadiens won the Stanley Cup was in the 1993 Stanley Cup Final against the Los Angeles Kings. Although, the Toronto MAPLE leafs are ten cups behind the Montreal Canadiens, the playing field has always been full of surprises and we do not know what this year might hold for the Toronto Maple Leafs.

How many rounds are in the NHL playoffs?

The NHL playoffs consist of four rounds, including the final. The first round has already been played and The Toronto Maple Leafs have secured the spot. The other teams that have advanced to this round are the Florida Panthers, the Washington Capitals, the Carolina Hurricanes, the Winnipeg Jets, the Dallas Stars, the Vegas Golden Knights and the Edmonton Oilers. Three Canadian teams have made it this far which is very impressive. The third round is called the Conference Finals which consists of a best-of-seven series, with the first team to win 4 games advancing to the finals. The Conference finals has 4 teams total, so the teams in the second round would go down in half. Finally. The Stanley cup finals would include the two teams with the most wins from the conference finals playing 7 games as well. The team with the most wins gets to take the Stanley Cup home. 

What is the schedule for the Toronto Maple Leafs in the second round of Stanley Cup playoffs?

Toronto will face the Florida Panthers 7 times during round 2, stamping the second time they face each other post-season in history. Their next faceoffs are in May 7, May 9, May 11, May 14, May 16, and May 18. Once the results for the games come in, the team with the first 4 wins will advance to the Conference finals. Torontonians are hoping to see their city rise up and dominate this round, but only the future will tell. Games usually start at 7:30 to 8, and go on for 60 minutes divided by 3 periods (each 20 minutes). The games do take longer than an hour as there are two 17 minute intermissions between periods. Ontario's sports bars and restaurants thrive during these games, with booked seats and tables by Leafs lovers across the province.

FAQs About the Toronto Maple Leafs and the Stanley Cup

How many Stanley Cups do the Toronto Maple Leafs have?

The Toronto Maple Leafs have won 13 Stanley Cups, with their last victory dating back to 1967.

When was the last time the Leafs won the Stanley Cup?

The last time the Leafs brought home the Stanley Cup was 58 years ago, in 1967.

What team has the most Stanley Cup wins?

That title goes to the Montreal Canadiens, who have won the Stanley Cup 23 times, the most in NHL history.

How many times have the Leafs made it to the Stanley Cup finals?

The Leafs have made it to the finals 21 times, winning more than half of those appearances.

Who are the Leafs playing in Round 2 of the 2025 playoffs?‍

The Leafs are facing the Florida Panthers in a best-of-seven series.

What are the Leafs' second-round game dates?

The scheduled games are on May 7, May 9, May 11, May 14, May 16, and May 18, with each team trying to get to 4 wins.

Go Leafs, Go!

As the Toronto Maple Leafs continue their 2025 playoff journey, the energy in the city is electric with hope and anticipation. With 13 Stanley Cups under their belt and a legacy that spans over a century, the Leafs carry both the weight of history and the dreams of millions of fans. While it’s been decades since their last championship win, this year feels different. Whether they go all the way or not, one thing is clear—Toronto is standing behind its team louder than ever. Go Leafs Go!