The 20 Greatest Maple Leaf Moments of the Last 20 Years

Listen people. I miss hockey, you miss hockey. There’s no use in complaining. We are where we are, and eventually things will be back to normal. Having said that, we could all use a little nostalgic therapy. There are plenty of great moments to relive.

I’ve been a Leafs fan since 1999. My dad watched every single game, and when I was six, he decided it was time to convert me to a hockey fan. I was a little resistant at first. I didn’t really understand it. But he was persistent. It was his pass time, and he knew that eventually I’d grow to love it. He took me to the rinks to watch junior and even minor hockey games. He introduced me to players, coaches, referees, and even the Zamboni drivers. Little did I know that one day, Zamboni drivers would be such a touchy subject for me. How different our world was 20 years ago. 

Nevertheless, I would imagine that if I had to ballpark it, I’ve watched about 85% of the Leafs regular season games since I was eight years old. That’s a lot of hockey. And hey, if you’re a Leafs fan reading this, I don’t have to tell you that a lot of those games were not amazing to watch. But sometimes you have to experience the bad times to really appreciate the good. It makes those moments so much sweeter. In those 20 years, the Leafs have had some incredible moments. I’ve decided to revisit what I feel are the 20 greatest on-ice moments of the last 20 years as a Leafs fan. Also, it will become abundantly clear why Senators fans hate the Toronto Maple Leafs so much.

Honorable mentions

  • April 16th 2001: Game 3 Eastern Quarterfinal, Cory Cross’ OT winner vs. OTT.
  • April 21st 2003: Game 6 Eastern Quarterfinal, Travis Green’s double OT winner vs. PHI.
  • April 12th 2004: Game 3 Eastern Quarterfinal, Ed Belfour’s 37 save shutout vs. OTT.
  • April 16th 2018: Game 3 Eastern Quarterfinal, Auston Matthews’ rips his first of the series past Tuukka Rask.

Number 20

April 3rd 2007: Bryan McCabe & the Leafs pull off a massive win vs. PHI to keep playoff hopes alive.

In the two years following the lockout, the Leafs were definitely okay. Sundin was still at the height of his game. Kaberle and McCabe were still putting up monster numbers offensively. Both years, the team seemed to have reasonable depth on the roster. In 2006-2007, the potential of a playoff team was there. However, inconsistency was the beast that killed this team. Separate eight and five game losing streaks in the span of 17 games left the Leafs fighting from behind down the stretch. Ultimately, they wouldn’t make the playoffs. But during the final week of the year, they were clinging to life after a solid run following the trade deadline. If they did not beat the Flyers on April 3rd, they would be mathematically eliminated. This game, at the time, was the biggest game for the Leafs since before the lockout. After blowing a 2-1 lead late, their patented Kaberle-McCabe-Sundin power play went to work in overtime, providing us with a cool moment and an all-time great Joe Bowen call.

Number 19

April 13th 2001: Game 1 Eastern Quarterfinals vs. OTT, Mats Sundin overtime winner.

The Leafs’ game plan against Ottawa in 2001 was clear: shut down their offense, and the rest will happen. After a near perfect sixty minutes of defensive hockey, captain Mats Sundin rewarded the team for their efforts by scoring on an absolute rocket in overtime. The Leafs gradually took the series over, and this was the first moment that it was apparent the Senators might be in trouble. I saw a 1-0 Leafs/Sens game in Ottawa once; the Leafs did not win.

Number 18

May 12th 2013: Game 6 Eastern Quarterfinals vs. BOS, Phil Kessel delivers.

I could go on and on about how much I loved Phil Kessel in Toronto. I won’t. But I will just let it be known I genuinely believe I was in the top 1 per cent of his supporters during his time in Toronto. Nevertheless, the Leafs needed to win that game 6 to go back to Boston. It was a rare solid defensive effort from the Leafs in game six, and after Phaneuf opened the scoring, Kessel followed it up by jumping on a loose puck to give the Leafs the two goal cushion. It was the dagger, as the Leafs won game 6 for their first home playoff win since 2004. Obviously, game 7 was painful. I’ve long believed game 7 wouldn’t be as painful if Game 6 hadn’t been such a masterpiece. But like I said: you need the bad times to appreciate the good, I guess.

Number 17

December 23rd 2019: Mitch Marner and the Leafs completely turn the game around in a matter of 59 seconds vs. Carolina.

Hey, you know these guys! Although we may never get to know the true worth of the 2019-2020 Maple Leafs, this moment will be remembered for a long time. In what was a sloppy game on both sides, it was one of the most emotional regular season games in a long time. These Christmas break afternoon games seem to always provide the entertainment. Mitch Marner scores twice, and he sets up Tyson Barrie for the other as the Leafs turn this game around in what was definitely the most interesting thing to happen in a Leafs/Hurricanes game in 2019-2020.

Number 16

April 8th 2017: Curtis McElhinney saves the game for Toronto.

In a season where the playoffs seemed like a best case scenario going in, the Leafs had a chance to clinch in game 81 on home-ice with Sidney Crosby and the Penguins in town. When Frederik Andersen exited with an injury, Leafs Nation went into a panic wondering if they’d even be able to clinch a playoff spot. A cold Curtis McElhinney entered off the bench and did what he does best: provide excellent relief. McElhinney robs Crosby in the last minute. If you’re a Leafs fan, this whole game had disaster written all over it. Instead, it was one of the greatest regular season periods I can remember a Leafs’ team playing in my lifetime. Holy Mackinaw, holy McElhinney.

Number 15

March 24th 2009: Curtis Joseph enters in relief and steals the show vs. Washington.

Many of you probably grew up in an era where the Leafs goalie was James Reimer, or Frederik Andersen. Some of you grew up in an era where it was Felix Potvin, or maybe even earlier. And some even grew up when it was like Martin Gerber or J.S. Giguere or some other interesting experiment. I’m still sad Olaf Kolzig never got into a game. But I grew up when it was Curtis Joseph, the first time. Although he wasn’t technically pretty to watch, few goalies were at the time. His knack for making timely saves was incredible. He was the type of goalie that with the game on the line, you could count on him. By 2008-2009, most of his magic was gone. His return to Toronto was nothing more than a good PR move. However, this moment would end up being one of his last NHL wins, and one of the last times I remember the ACC (or Scotiabank Arena) being this loud for a regular season game. Ovechkin was absolutely on fire that night, but CuJo really didn’t care. It was essentially a meaningless game for the Leafs that in the end had a ton of meaning.

Number 14

May 4th 2004: Game 6 Eastern Semifinals, Darcy Tucker destroys Sami Kapanen.

Probably my favourite hit of all-time, if you’re into that sort of thing. After Mats Sundin ties the game late in the third, the overtime period of game six is one of the craziest in the pre-lockout era NHL. This hit added to the chaos, and seemed to swing anything that was left of the Flyers’ momentum in the Leafs’ favour. It is truly amazing that the Leafs end up losing this game considering the period and a half they had of just purely taking over this game. C’est la vie. 

Number 13

April 15th 2019: Game 3 Eastern Quarterfinal, Mitch Marner double shot block to secure game.

I will die on the hill of believing that the Leafs were the better team in this series against Boston, and that they squandered several opportunities to seal the series. No matter what, they were absolutely dialled in for game three. Boston had a late charge, and Mitch Marner decided to lay his body on the line in the final seconds to help the Leafs seal the 2-1 series lead. It was a moment from the new era Leafs that reminded me of something Gary Roberts or Darcy Tucker would’ve done in the early 2000’s. Mitch has a lot of great moments left in him, but this one officially entered him into the library of great Leafs memories.

Number 12

February 21st 2009: Mats Sundin returns to Toronto.

The legend Mats Sundin returns to Toronto and gets the reception he deserves. I’ve jokingly referred to the ACC as “The House That Mats Built” but in reality, he was up until that point the greatest athlete to call that building home. The way everything played out at the time was unfortunate, but this was his night and he delivered perfectly. He never got the proper sendoff, but this moment seemed to do him justice, even if he was wearing the wrong jersey.

Number 11

May 28th 2002: Game 6 Eastern Conference Final, Mats Sundin ties the game vs. CAR with 20 seconds left.

One of my favourite Bob Cole calls of all-time; “so we’re tied, what else is new.” The Leafs’ had been clinging to life since their Game 4 loss put them down 3-1 in the series. After a 1-0 win in Game 5, the Leafs’ were trying desperately to force a Game 7. Of course, the clutch captain would step up, and tie the game 1-1 to force overtime. Unfortunately, Martin Gelinas scored the game winner in OT to eliminate the Leafs. But that anticipation all game for the Leafs to get that goal was crazy. When they finally got it, Leaf fans everywhere were jumping around their livingroom. Or at least I was.

Number 10

April 15th 2017: Game 2 Eastern Quarterfinals, Kasperi Kapanen OT winner

If there’s one thing Kasperi Kapanen seems to have a knack for, it’s scoring clutch goals. The rookie buried a perfect pass from Brian Boyle to give the Leafs an improbable win in Game 2 to even the series going back to Toronto. I’m not going to lie, I went bowling with friends during overtime. It was on at the bowling alley, but quite honestly I had zero belief they’d win this game. They did it. I will never forget abandoning bowling, watching the replay on my phone, and proceeding to drink way too many beers with the other Leaf fans I was with that night. Thanks for the excuse to drink beers Kasperi!

Number 9

April 16th 2018: Game 3 Eastern Quarterfinals, Frederik Andersen stick save on Pastrnak.

The craziest playoff save I can remember as a Leafs’ fan. (Insert the “thats cause they never make the playoffs” joke here). With the game on the line, Andersen makes a completely non-sensical save. The more I watch it, the less I believe it actually happened. If the Bruins score there, the series could have been much shorter. 

Number 8

April 27th 2000: Game 1 Eastern Semifinals, Wendel Clark standing ovation.

When Wendel Clark returned for his third and final stint as a Maple Leaf, he was older and broken down. However, he was fantastic in game one of the Eastern Semifinal against the Devils. He assists on Darcy Tucker’s (eventual) winning goal, and a few shifts later fired a shot off the post. Leaf fans gave him an ovation that lasted into and through the TV timeout. For you young Leaf fans, it is important to note that once upon a time, the ACC was the loudest building in the NHL, and that Wendel Clark represented the heart and soul identity that the Leafs’ were built on. I’m sure you can understand why 25-49 year olds are so nostalgic about those times.

Number 7

May 6th 2013: Game 3 Eastern Quarterfinal, Jake Gardiner scores first home playoff goal in Toronto in nine years.

Nine years of frustration, outside and inside the Air Canada Centre completely expelled from one Jake Gardiner shot. As someone who waited nine years for this goal to happen, I can’t tell you how good it felt to hear that Leafs’ crowd during a playoff game again. The Leafs’ would ultimately lose the game, but this goal was symbolic for Leaf fans. After all the incompetency and inept decisions, for one minute none of it mattered. People point at Gardiner’s struggles in Game 7’s, and some of that is justified. But he did score one of the coolest goals of the last 20 years.

Number 6

May 4th 2002: Game 2 Eastern Semifinal, Gary Roberts triple overtime winner.

Nine year old me stayed up way past my bedtime for this one. Completely worth it. It was one of those games that eventually got quieter and quieter, and generally that’s good news for the road team. Not this time. As you will see in the top five, the Leafs’ have always had Ottawa’s number in the playoffs. This was a game where the Sens were set up to take a 2-0 series lead back to Ottawa. This goal completely changed the complexion of the series. Also worth noting: Walter Gretzky lookin’ good.

Number 5 

April 20th 2004: Game 7 Eastern Quarterfinal, Joe Nieuwendyk scores identical soft goals on Patrick Lalime.

Even Pat Quinn almost celebrated. The previous season, Patrick Lalime finished fifth in Vezina voting. He was widely considered as one of the best goalies in the NHL. The Leafs thought that best case scenario, three goals against him should be enough to win the game. By the start of the second period, Martin Prusek was in net for the Senators. Nieuwendyk scored two nearly identical goals after Chad Kilger opened the scoring, and that was basically it for the Senators as the Maple Leafs’ eliminated them from the playoffs for the fourth time in five years. Harry Neale does a great job absolutely ripping the Senators as well. Neale was underrated for sometimes being very blunt. It was great.

Number 4

October 14th 2006: Mats Sundin’s 500th goal.

This is partly why 2006-2007 was a painful year to miss the playoffs. New coach, newish roster, but Mats was still up to his old glorious moments; none greater than this in the very early stages of the season. After Darcy Tucker got called for hooking with eight seconds left in the 3rd period, Sundin wasn’t happy. It was a rare occasion where he was giving it to the referees. He decided to take matters into his own hands, and scored a shorthanded goal, his third of the night for 500 goals on his career. I know Mats played for Quebec to start his career, but he was the greatest Maple Leaf of the last thirty years at the time. It felt like we had been there with him every step of the way. We had seen most of those 500 goals come in the Blue and White Maple Leaf jersey. This goal came in just the most spectacular fashion you could ask for. As a Paul Maurice fan, one of my favourite moments of this clip is when it finally occurs to him that it was Mats’ 500th, and starts clapping. Very, very cool.

Number 3

April 18th 2001: Game 4 Eastern Quarterfinal, the Leafs sweep the Senators.

The Leafs had beaten the Senators in the playoffs the year prior, but expectations were different this time around. The Senators finished with 109 points, while the Maple Leafs just snuck into the playoffs with 90 points. The Senators won the season series 5-0. Everything pointed to things being different this time around for Ottawa. Instead, head coach Pat Quinn matched Shayne Corson up with Alexei Yashin, and Corson stuck to Yashin like glue for four games. It was more than enough to stifle the Senators offense, and the Leafs pulled off one of the best upsets in the last 20 years. The way that momentum gradually shifted in the Leafs favour over the series makes this game a classic. Going into Game 4, the sweep felt inevitable. The Senators opened the scoring early, but the Leafs took over soon after. The game was more like a celebration than it was a game. Groovy, baby. 

Number 2

April 22nd 2000: Game 5 Eastern Quarterfinal, Steve Thomas ties and wins the game.

With the series tied 2-2, this was hands down the pivotal point of the series. If the Leafs don’t tie this game, it’s very possible the early 2000 Maple Leafs end up looking very different. When Steve Thomas scored these two goals, he set the table for the team moving forward. The Leafs eventually win game 6 and the series, but these goals came during a high action third period, and one of the craziest 5-on-5 overtimes I’ve ever seen in my life. Steve Thomas is known as the definition of clutch in the hockey world. This game is among his finest work, finishing off a crazy back and forth sequence. 

Number 1

October 12th 2016: Auston Matthews puts up four in his first game.

It seems impossible now, but it happened. There was plenty of hype about Auston Matthews. But generally speaking, the consensus seemed that he was going to be a solid two-way forward. He could score goals, but we didn’t know how good of a goal scorer he actually would become. With the greatest single first game in history, Matthews puts four goals up on the Ottawa Senators. I think it’s safe to say that Auston is currently the most prized possession for Leaf fans, and he made his presence known from the moment he stepped foot on the ice as a Maple Leaf. Auston Matthews, baby.

Did we miss any moments? Let us know in the comments below.

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Brutes Battaglia

Former writer for Puck77. Life long Toronto Maple Leafs fan. I also enjoy all things New England Patriots, Toronto Raptors, and Boston Red Sox. Diehard Third Eye Blind fan.

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