Cleveland Cavaliers and Toronto Raptors Add To Exceptional Playoff Legacies

Toronto Raptors forward RJ Barrett (9) celebrates as Cleveland Cavaliers guard Donovan Mitchell (45) tries to walk away during the second half of game three of the first round of the 2026 NBA Playoffs at Scotiabank Arena.

The Cleveland Cavaliers are trying to win a championship, and their first step is their series against the Toronto Raptors. While the Cavaliers started the series with two wins, the Raptors responded with victories of their own. Now, both teams have a shot at advancing to the next round, and it comes down to who wants it more.

While it has been a while, this is not the first time the Cavaliers and the Raptors have met in the playoffs. The postseason history between these two teams goes back to 2016, and that was a significant year for both teams. With that said, step into a time machine and explore the past matchups between these teams.

Cavaliers And Raptors Fight For the Top Spot

In 2016, the Cavaliers were the top team in the Eastern Conference. They finished that season with a record of 57-25, and the Raptors were right behind them, as they were 56-26 that year. Both teams played well during their playoff runs, as Cleveland defeated the Detroit Pistons and the Atlanta Hawks in their first two rounds.

The Raptors beat the Indiana Pacers and the Miami Heat early on. Then, the Eastern Conference Finals came down to the Cavs and the Raptors, and Cleveland came out victorious. The Cavaliers beat them 4-2, and they faced the Golden State Warriors in the NBA Finals.

The series against the Warriors was historic, as the Cavaliers won their first championship. That series involved the 3-1 comeback, and in the last game of the series, the Cavs beat the Warriors 93-89, and LeBron James had 27 points.

Cleveland bounced back from the previous year, as Golden State won it all for the first time since 1975. The Warriors’ 2015 win led to Kevin Durant winning a title, and since then, the franchise has won three more championships.

Cavaliers and Raptors Meet Again

The Cavs and the Raptors’ playoff rivalry continued, as they met in 2017. Cleveland was second in the Eastern Conference that year, and Toronto was third. The Boston Celtics were on top of the East that year, and they finished the season with a record of 53-29.

When it came to that year’s postseason, the Cavaliers beat the Pacers in the first round. They swept them, and right after that, they swept the Raptors. Then, after beating the Celtics, the Cavs found themselves back in the Finals. However, that was one of the instances where the Warriors won it all.

In 2018, the Cavs and the Raptors faced each other again, and Cleveland came out victorious. Toronto was the top team in their conference that year, and they had a record of 59-23. However, after beating the Washington Wizards in the first round, the Cavaliers swept them.

Cleveland’s playoff journey continued, and after beating Boston, the franchise reached the Finals once again. Golden State won another title, and after that season, James joined the Los Angeles Lakers.

Will Cleveland Add To Its Legacy?

Cleveland Cavaliers guard Donovan Mitchell (45) drives.
Apr 20, 2026; Cleveland, Ohio, USA; Cleveland Cavaliers guard Donovan Mitchell (45) drives on Toronto Raptors forward Sandro Mamukelashvili (54) during the first half during game two of the first round of the 2026 NBA Playoffs at Rocket Arena. Mandatory Credit: David Dermer-Imagn Images

Both the Cavaliers and the Raptors are championship-winning franchises, and this year is a chance to add to that legacy. This year’s playoffs have been exciting, and there are teams capable of winning it all. With the backcourt duo of James Harden and Donovan Mitchell, the Cavs cannot be counted out.

This year is an opportunity, and in what is their first playoff series against the Raptors since 2018, they have to play at a high level. The Raptors are giving them trouble, and while time has passed, a win over the Cavs would be redemption for their previous postseason matchups. Toronto is on a mission, and in what has been a competitive series, Scottie Barnes and his teammates are giving the Cavaliers a run for their money.