Donovan Mitchell, James Harden, Evan Mobley, and the Cleveland Cavs will look to build on their 4-0 best-of-7 series loss to the New York Knicks in the 2026 Eastern Conference Finals, proving they are title contenders in key games amid the 2026-27 season. When Harden agreed to a $97 million Cavs extension, it kept Cleveland in the mix among the upper echelon of a competitive Eastern Conference.
Harden’s signing followed the Cavs’ landing of Peyton Watson in a sign-and-trade, adding an intriguing layer to their starting lineup. Watson, a young 3-and-D forward, gives the Cavs a strong perimeter defender who averaged 14.6 points and 4.9 rebounds while making 41.1% of his 3-point attempts in his fourth season with the Denver Nuggets.
In a stacked Eastern Conference, the Cavs have won 50+ games in three of the last four seasons but will look to take the next step toward becoming one of the NBA’s best teams in 2026-27. To gauge where the 2026-27 Cavs stand in their chances of winning a title amongst marquee games, here are four must-see matchups to keep in mind ahead of the upcoming season.
Cavs’ Eastern Conference Finals rematch (Nov. 7)
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In their first meeting since the Knicks sent them home in Game 4 of the Eastern Conference Finals, the Cavs will have a chance to avenge that loss in the regular season. Against the defending champion Knicks, this is their first chance to show just how much they’ve improved since then.
Given that 2026-27 will be the first full season for James Harden and the Cavs, expectations are higher than ever. The Knicks, who went on to beat the Spurs, 4-1, in the 2026 Finals, are the team to beat this upcoming season. However, the Cavs are good enough to stay afloat in a competitive Eastern Conference and return to the ECF.
If they’re to meet in a playoff rematch in 2027, the Cavs will have a better understanding of where they stand after a 4-0 sweep at the hands of the defending champions. Then, the Knicks will host the Cavs at Madison Square Garden four days later on November 11.
Cavs host defending West Conference champion Spurs (Dec. 15)
In a potential early NBA Finals preview, the Cavs will host the defending Western Conference champion Spurs on December 15. For a team with championship aspirations, this is a great opportunity for the Cavs to send a message to the Spurs, who feature the towering 7-foot-4 Defensive Player of the Year, Victor Wembanyama.
The Spurs have an array of young, dynamic score-first guards, led by Stephon Castle, Dylan Harper, De’Aaron Fox, and Devin Vassell. For a team that finished in the bottom half of defensive efficiency last season, the Cavs must improve on that end of the floor if they plan to return to the Finals for the first time since 2018.
And adding Peyton Watson undoubtedly addresses the Cavs’ perimeter defense. In contrast, James Harden, who was still playing for the Clippers during the Cavs’ only two meetings against the Spurs last season, adds a new wrinkle to this intriguing showdown 10 days before Christmas Day.
Cavs face Pistons in MLK matinee matchup (Jan. 18)
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The Pistons made a 14-win jump to win 60 games to lead the Eastern Conference standings last season. In a grueling seven-game series against the Pistons in the second round of the playoffs, the Cavs’ 125-94 Game 7 victory punched their ticket to the Eastern Conference Finals.
While the Cavs added Peyton Watson and Cam Whitmore in a multi-team trade that sent Dennis Schroder to the Hornets and Max Strus to the Clippers, the Pistons added John Collins to their frontcourt to replace Tobias Harris, who signed with the Spurs via free agency.
The Pistons also landed Taurean Prince and Gary Harris as part of their six-team blockbuster trade for Collins, while parting ways with Isaiah Stewart, Caris LeVert, and Marcus Sasser. The Cavs’ elimination of the Pistons in the second round of last year’s playoffs triggered these changes. Now, it’s time to see which team improves most between the two.
Cavs host 76ers on March 1
When the Cavs host the 76ers on March 1, both teams will be much more established than they were in their first meeting on October 22, the Cavs’ first game of the regular season. While an NBA Cup matchup between the two is scheduled for November 6, the 76ers’ road game in Cleveland will give fans a better idea of where they stand.
The 76ers are coming off perhaps their best offseason in franchise history, trading for Jaylen Brown in exchange for Paul George, signing LeBron James, Anfernee Simons, and Dean Wade this summer. This is an opportunity for the Cavs to send a message.
Not only for the rest of the NBA, but to LeBron, as a means of saying he made a mistake in choosing to sign with the 76ers rather than return to the Cavs, the team that he led to their first title in franchise history in 2016.