The 2026-27 regular season schedule has been released, and it isn’t necessarily kind to the Cleveland Cavaliers. They have 16 sets of back-to-backs — which is tied for the most in the league. On top of that, their schedule is incredibly difficult out of the gate, with most of their marquee matchups happening in the first two months of the season.
With that in mind, let’s run through the 10 games I’ll be looking forward to most this season.
10. March 1 vs. 76ers
We could get into all the storylines that make games with the Philadelphia 76ers must-watch TV. However, those aren’t necessarily what make this matchup interesting.
Cleveland’s schedule is front-loaded. As such, there aren’t many opportunities against great teams down the stretch, aside from a few West Coast games during their annual MAC Tournament road trip at the beginning of March.
This game against the Sixers will serve as a good litmus test for where the Cavs are at this point in the season. It comes a few weeks after the trade deadline, meaning both teams should have their playoff rosters set. And, it’ll be far enough away from the end of the regular season where teams start resting players. As such, we should get a good preview of what could be a playoff matchup.
9. Jan. 5 vs. Raptors
The Toronto Raptors pushed the Cavs to the brink last postseason. This upcoming season, they should be even better — assuming the Kawhi Leonard deal actually goes through.
This will be their first of four meetings. Toronto proved to be a tough matchup for the Cavs last season. Will that still be the case by the time they meet in the middle of next regular season?
8. April 1 vs. Celtics
The Boston Celtics only come to Cleveland once this upcoming season, and we have to wait until the very end of the year for that to happen.
Late-season matchups can be great tests or completely inconsequential. We won’t know which one this will be until right before the game. But this has the potential to be a preview for what we could see in a postseason series.
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7. Nov. 20 vs. Pacers
We never got to see a rematch of the Cavs and Indiana Pacers after their 2025 playoff series. Tyrese Haliburton missed all of last season with injuries, causing Indiana to go from title contenders to a lottery team.
This upcoming season’s Pacers won’t resemble that 2025 team much. Myles Turner and Bennedict Mathurin aren’t in the picture anymore. Instead, they will be built around a much more imposing front line featuring Ivica Zubac.
This will also be an important NBA Cup group stage game. I know the in-season tournament doesn’t mean much, but it would be encouraging to see the Cavs fare well in a difficult group with the Sixers, Pacers, and New York Knicks.
6. March 9 at Pistons
This will be the Cavs and Detroit Pistons’ final matchup of the season. Last year, they met in the playoffs for a seven-game series. Could the same happen this upcoming year?
5. Nov. 29 at Knicks
The Cavs play the Knicks four times before Christmas. This matchup will actually be their third time facing off.
Each of Cleveland’s home games are the second leg of a back-to-back, so I’m not going to highlight either of those. I chose this late November meeting over their first trip to Madison Square Garden because it’ll be an NBA Cup group stage game.
Again, whether or not you think the in-season tournament matters is up to you. What I will say is that it would be meaningful if the Cavs could advance out of the group stage for the first time in franchise history. And as the Knicks showed last year, winning the NBA Cup can actually lead to playoff success.
4. Dec. 15 vs. Spurs
Victor Wembanyama has only played in Cleveland once during his career and is winless in three total meetings. We’ll see if that changes when the Cavs host the San Antonio Spurs for their annual trip.
Wemby vs. Cleveland’s frontline of Jarrett Allen and Evan Mobley is an intriguing matchup. Both Allen and Mobley have size and speed to make life difficult for Wemby. That’s incredibly important in a league that could be dominated by Wemby for the next decade.
3. Dec. 31 vs. Clippers
Darius Garland made a huge impact on the Cavs during his seven seasons here. He helped turn what was a rudderless team when he was drafted in 2019 into a legitimate championship contender. This includes being the lead ball handler for the 2024-25 team that put together the second-best regular-season record in franchise history.
This will be Garland’s first game back in Cleveland since he was traded away for James Harden last deadline. Seeing him back in Cleveland will be bittersweet, even if the marriage ending when it did was best for both sides.
2. Oct. 22 at 76ers
The adrenaline is always a little higher on opening night. It coinciding with LeBron James’s first home game with the Sixers should up that even more.
There were presumably many in the organization who thought LeBron would sign with Cleveland at some point this summer. His spurning them for a conference rival likely makes this sting worse. Fortunately, the Cavs won’t have to wait long to show James that he made the wrong choice.
1. Nov. 6 vs. 76ers
LeBron’s annual visit over the last eight years has served as an opportunity for Cleveland to show their hometown hero how much he means to them. That joyous atmosphere won’t be here when he returns this time around after he chose to likely end his career with a conference rival instead of his hometown team.
There won’t be close to the anger and vitriol there was for James’s first game in Cleveland as a member of the Miami Heat in 2010. However, there will be more than a handful of boos, which would’ve been hard to fathom at this time last year.
On top of that, this will be another matchup between two of the top teams in the East and an NBA Cup game. If the Cavs want to advance in the group stage, they’ll likely need to take care of business here.
Which game are you most looking forward to this season? Let us know in the comments below.
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