With the glory of Kawhi’s shot and the second round now behind them, the Toronto Raptors will advance to their second-ever Eastern Conference Finals against the Milwaukee Bucks starting on Wednesday. The Bucks are the No. 1-seed with their own heavyweight showstopper Giannis Antetokounmpo which should present a tough, but outstanding match-up. The series winner will go on to the NBA Finals.

While Toronto’s playoff history is a mixture of heartbreak and hope, trials and triumph, after 24 years in the NBA this might just be the year of the Raptor.  

Here’s a countdown of the top 7 moments in the team’s playoff history. 

7. The First Taste of Success (2000)

Vince Carter, Toronto Raptors 200 Eastern Conference

While the NBA has been around since 1946, the Raptors weren’t founded until 1995. Inevitably, the team faced growing pains of a new franchise trying to find their place — until 1999. Enter the Vince Carter Era.

During the 1999-2000 season, Carter —playing alongside his cousin Tracy McGrady— brought Toronto to their first ever Eastern Conference playoff appearance. With the newbie Raptors ranked as a No. 6-seed against the No.3-seed New York Knicks, the 3-0 loss didn’t come as a shock. But this wasn’t about winning or losing, it was a historic moment that helped put the team on the map.

6. Back With Vin-gance (2001)

Vince Carter, Toronto Raptors against the NY Knicks

Call it déjà vu. After closing out the 2000-01 season with a then franchise-record 47 wins (currently it’s 59), the Raptors were back face-to-face with the Knicks for a rematch in the Eastern conference quarterfinals. Despite losing the first and third games of the series, the Raptors ended all doubt when they pulled off a final Game 5 win. The 93-89 victory knocked out the Knicks and made history as the first playoff series win for the team, advancing them for the first time to the Eastern Conference semifinals against the Philadelphia 76ers. 

Vince Carter slam dunks

5. 50 Reasons to Remember (2001)

The Raptors first semifinals appearance was one for the books. With the Raptors sitting as the No.5-seed, there was chatter of the No.1-ranked 76ers making easy work out of the team, but Toronto had other plans. The second round became an epic duel of sorts, with the Raptors winning three games pushing the 76ers to a full best-of-seven series — but Game 3 is the one to remember.

On the heels of their Game 2 loss, Vince Carter hit the court with purpose and put on a show-stopping performance scoring an explosive 50-points. His contributions didn’t stop at just the basket; Carter had 6 rebounds, 7 assists, and 4 blocks, ultimately leading the team to a Game 3 win of 102-78. He remains the only Raptor to score 50 points in a postseason game. Despite losing in Game 7, Carter’s performance was emblematic of the height of Vinsanity and goes down in Raptors history as one of the best individual playoff performances. 

4. The Ball That Didn’t Fall  (2001)

The team had just faced two consecutive losses but managed to pull off a 101-89 victory in Game 6, entering the seventh and final showdown against Philadelphia ready to put it all on the line. They trailed for most of the first half, entering the second half down 50-42. In the third quarter, they put up a solid 24 points which closed the gap to a 69-66 lead for Philadelphia, and they took that momentum with them into the fourth. With 55 seconds left on the clock, Toronto Raptor Dell Curry drained a 3-pointer bringing it to a one-point game: 88-87 for Philadelphia.

Then, one of the most heartbreaking moments in playoff history happened.

With two seconds left in the game, Curry inbounded to Carter. Philadelphia forward Tyrone Hill was tight on him, Carter pump-faked, gaining a clear shot. With 1.3 seconds left, Carter put up his infamous jumper — this was make or break.

As the ball hit the rim and bounced off, the buzzer sounded. The end. Toronto’s playoff journey was over, and fans across the city felt the pain of a “What if?” moment that still resonates today.

3. Lowry’s Heave of Faith  (2016)

The years following the Raptors trip to the second round in 2001 were filled with heartbreak. The team was knocked out consistently in the first round in 2002, 2007, 2008, 2014, and most painfully, a sweep at the hands of the lower seed Washington Wizards in 2015. These heartbreak years had earned the team a reputation of being a “choke” team who would only find success in the regular season — but that was about to change.

It was Game 1 of the conference semifinals, Miami was up 90-87 with only 3.3 seconds left on the clock when Kyle Lowry received the inbound and took the ball up to half-court. With only 1 second left, he fired a heroic shot to tie the game and force an OT. While the Raptors eventually lost Game 1 in OT (102-96),  they went on to win Game 7 in double over time (116-89). This series win was historic as it allowed the Raptors to advance to the Eastern Conference Finals for the first time in franchise history. 

2. Making History in The Finals  (2016)

LeBron James argues with Toronto Raptors

For the first time in 20 years the Toronto Raptors advanced past the second round and entered the Eastern Conference Finals against the Cleveland Cavaliers. After losing the first two games in the series, Toronto fought back and pulled out two consecutive wins, with DeRozan and Lowry putting up 67 of their 105 point victory in Game 4 (105-99). Despite their best efforts, the Cavaliers went on to win both Game 5 and 6 with precision. This was the closest Toronto came to climbing Everest. 

1. The Shot Heard Around The World  (2019)

Heroic. Historic. Legendary. That’s what the Raptors Game 7 against the Philadelphia 76ers was. 

The playoff series was the first against Philly since the heartbreak of 2001. After six hard-fought games in the Eastern conference semifinals, both teams put up a valiant effort in the final matchup.


It was 88-89 for Toronto with 10.8 seconds left on the clock and Kawhi Leonard was at the foul line. The first shot went in: now 90-88 for Toronto. His second shot fell short, Philadelphia took the rebound resulting in a layup from Jimmy Butler to tie the game 90-90 with 4.2 seconds remaining — And then the incredible happened.

On inbound, Kawhi took the ball along the inside of the three-point line to the corner, heavily guarded by Philadelphia’s Ben Simmons and Joel Embiid. With only 0.5 seconds left in the game, Kawhi fired up a fadeaway shot from the corner baseline. The arena froze. Four bounces on the rim and it’s in. The crowd erupted like an earthquake. Raptors won 92-90, with the first ever game-winning buzzer-beater in a Game 7. 

Kyle Lowry said it best in his postgame interview: “2001, it didn’t fall for Vince. 2019, it fell for Kawhi.”

Share on facebook
Share on twitter
Share on email