5 Most Difficult Games on Cleveland Cavaliers 2026–27 Schedule

The Cleveland Cavaliers finished the 2025-26 season with a record of 52-30, and now, they are getting ready for another journey. Cleveland's schedule was released, and Donovan Mitchell and his teammates will look to match or surpass last year's total. However, it will be a challenge.

Teams around the league improved, and the biggest move of the offseason involved an Eastern Conference rival. Now, the Cavaliers are trying to make at least one move before the start of the season. Whether they make a move or not, the Cavs have their work cut out for them, and throughout the season, they will have tough games. So, here are a few games to watch out for.

Cavs Taking On Eastern Conference Contender (Oct. 22)

Cleveland will start its season off with a bang, as the year begins with a road game against a conference rival. The Cavs will face the Philadelphia 76ers, and a few familiar faces will be in action. Philadelphia signed Dean Wade at the start of free agency, and as time passed, they added LeBron James.

James and the Sixers are a contending team, and getting an early win could be the start of a successful season. The same can be said for the Cavaliers, as a win over the 76ers may be what they need to build momentum.

The Cavaliers will face the Sixers throughout the season, but this game means more. When it comes to road games, getting a win is difficult. It is even tougher when it is the first game of the season. However, if the Cavs pick up a victory, they make a statement. It shows that they can still compete with elite teams, and as time goes on, they can put themselves in a position to win it all.

Cleveland Faces Western Conference Threat (Nov. 4)

In the second month of the season, the Cavaliers will face an exceptional team. They will face the Oklahoma City Thunder, and the first matchup takes place in Cleveland. Then, Cleveland travels to Oklahoma City a few days later.

The Thunder finished the previous season with a record of 64-18, and they were first in the Western Conference. Before that, they won a championship after beating the Indiana Pacers. Shai Gilgeous-Alexander was crowned MVP last season, and this season is a chance to win three in a row. He and the Thunder are on a mission, and stacking wins could help them return to the NBA Finals.

The Cavaliers struggled against the Thunder last year, as Oklahoma City swept the season series. A road win against them could tie the series or win it depending on the outcome of the previous game. Regardless, the Cavs have their hands full with a championship-winning team.

Cavs And Knicks Meet Again (Nov. 11)

Cleveland defeated the Toronto Raptors and the Detroit Pistons during its playoff run, but series against the New York Knicks was a different story. The Knicks beat the Cavs 4-0, and they beat the Spurs to win it all.

The Cavs' series against the Knicks started on the road, and despite having a lead, Cleveland lost Game 1. The Cavaliers did not recover from that, and they were sent home after another big loss. This year, they can put the past behind them, and the season series against New York is a good start.

In what will be the second game of the season series, the Cavaliers can get a win in Madison Square Garden. If so, that is something that can help them in the long run.

Cavs Battle Young Western Conference Squad (Dec. 15)

The Spurs were second in the Western Conference (and the league) last season, and Victor Wembanaya led the way. Then, San Antonio also has young players such as Stephon Castle and Dylan Harper that make the team even better.

San Antonio's core got its first taste of the Finals, and while things did not go in the team's favor, it was a learning experience. This group will only get better, and they are a threat teams cannot take lightly. Cleveland will get its first glimpse of this team in December, and it is a home game. The Cavs can get a win over another contending team and show they have what it takes to succeed.

Cleveland Hosts Playoff Foe (Jan. 5)

Cleveland's playoff journey was not easy, and it all started with a seven-game series. The Raptors gave the Cavs a scare in the first round, and players like Scottie Barnes and RJ Barrett played a role. Toronto made a move during the offseason, as the franchise sent Brandon Ingram, Gradey Dick and draft picks to the Los Angeles Clippers for Kawhi Leonard. However, the deal is pending due to an investigation.

Despite that, the Raptors are still a legit team, and they can give the Cavs trouble. So, getting a win in the first meeting could help Cleveland set the tone.

The Cavs have a big year ahead of them, and these matchups and more are worth keeping an eye on.