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The Raptors were tied for the Philadelphia 76ers with only a few seconds left in regulation time of the seventh game.
Jimmy Butler had tied the score in the final moments with a lay-up, which apparently led the game to overtime since the 76ers then made a mistake on Leonard.
With a remaining possession and a score of 90-90, Leonard received the ball at the edge of the three-point area before dribbling his opponent to the corner and firing an unbalanced shot.
The ball bounced four times on the rim before sinking into the basket after the ring, leading the Raptors to the Eastern Conference finals.
The crowd in Toronto was sent to bed, while fans gathered on the field to celebrate with Leonard and the rest of the team.
The Raptors will now advance to the Eastern Conference finals against Milwaukee Bucks, who dismantled the Boston Celtics in five semifinal matches.
Leonard was an outstanding performer for the playoff Raptors in his first year in Toronto.
The striker averages 31 points per game, with 3.6 assists and 6.6 defensive rebounds.
Last year, he played only nine games after being injured. He admitted after the match that he had struggled to cope with his final year with the San Antonio Spurs.
"It made us feel good, we work every day on this basis.
"I missed the last one, it was short, so I just wanted to put it in the air and it bounced the shooters.
"Dude, it's a lot of work, I just pulled as hard as I could.
"I just tried to play hard in each possession, I just wanted to leave everything on the field in case we ran out of tonight.
"Last year was very bad for me. I was going through a lot of things with everything that was going on.
"God is good, I prayed every day and I am healthy and able to play basketball.
"You can just see what it does for you.
"The Bucks are a very good team. They led the league this year. Only team with 60 wins, it's a tough match. Hope this game of seven has prepared us for them. "
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