Honestly, if you grew up a Cavs fan in the late '80s or '90s, the sight of a red jersey probably still makes your eye twitch. It’s that deep. The Cleveland Cavaliers vs Chicago Bulls matchup isn’t just another date on the NBA calendar; it’s a decades-long saga of "what ifs" and "not agains."
We’ve seen it all. Michael Jordan hanging in the air over Craig Ehlo. LeBron James staring down a United Center crowd. And now? We have a 2025-2026 season where the dynamics have shifted into something weird, unpredictable, and surprisingly high-scoring.
Back in December 2025, things got spicy. The Bulls took two straight from Cleveland in a span of three days. On December 17, Josh Giddey—who’s been a triple-double machine lately—put up 23 points, 11 boards, and 11 assists to lead Chicago to a 127-111 win. Two nights later, they did it again, dropping 136 points on a Cleveland defense that usually prides itself on being a brick wall.
The Lonzo Ball Factor and the Trade That Shook the I-90
The off-season before this 2025-26 run was a bit of a soap opera. In July 2025, these two teams actually sat down at the negotiating table. That’s rare for rivals. Cleveland sent Isaac Okoro to the Windy City, and in return, they got Lonzo Ball.
Yeah, that Lonzo Ball.
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It was a massive gamble for Cleveland. They wanted the playmaking and the "3-and-D" potential, even with the injury history. Meanwhile, Chicago got Okoro, a guy who basically eats, sleeps, and breathes perimeter defense. Seeing Okoro in a Bulls jersey while Lonzo suits up in the Wine and Gold is still tripping people out.
In that December 20th game, Darius Garland went absolutely nuclear, scoring 35 points. But here’s the kicker: Donovan Mitchell was out with an illness. Without "Spida" to balance the floor, the Bulls’ depth just overwhelmed them. Matas Buzelis—the rookie who’s quickly becoming a fan favorite in Chicago—dropped 24. Nikola Vučević added another 24 and snatched 15 rebounds.
It’s a different kind of Bulls team. They aren't just relying on one superstar; they are moving the ball, shooting 52% from the field, and basically sprinting teams into the ground.
Why the Cleveland Cavaliers vs Chicago Bulls Rivalry is Different Now
For the longest time, this rivalry was defined by the "Jordan Era" dominance or the "LeBron Era" revenge. But look at the standings right now. As of mid-January 2026, Cleveland is sitting at 23-19, fighting to stay in the upper echelon of the Eastern Conference. Chicago is right on their heels at 19-21.
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It’s a battle for the middle. That sounds boring, but in the NBA, that’s where the real desperation happens.
Recent Matchup Reality Check
- Dec 17, 2025: Bulls win 127-111 (Giddey triple-double).
- Dec 19, 2025: Bulls win 136-125 (Garland drops 35, Mitchell out).
- Nov 8, 2025: Cavs win 128-122 (A tight one at Rocket Mortgage FieldHouse).
Cleveland has been struggling with consistency. One night they look like world-beaters, and the next, they give up 136 points to a Chicago team that's sub-.500. It’s frustrating for fans. Coach Kenny Atkinson has been tinkering with the lineups, even benching De’Andre Hunter recently to find a spark.
Chicago, on the other hand, is playing "spoiler." They don’t have a Top-5 MVP candidate, but they have five or six guys who can give you 15 to 20 points on any given night. Kevin Huerter has been a sneaky good addition, stretching the floor and keeping defenses honest.
Ghosts of Playoffs Past
You can't talk about Cleveland and Chicago without mentioning "The Shot." May 7, 1989. Richfield Coliseum.
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Cleveland had swept the Bulls in the regular season that year. 6-0. They were the better team on paper. But Jordan didn’t care about paper. That hanging jumper over Ehlo didn’t just win a game; it broke the spirit of a generation of Cleveland sports fans.
Then came the LeBron years. That was the era of the Cavs finally punching back. Whether it was the 2010 first round or the 2015 semifinals, LeBron seemed to have a personal vendetta against the Bulls. Remember his buzzer-beater in Game 4 in 2015? That was the ultimate "right back at ya" to the ghost of Jordan.
What to Expect Next
If you're looking at the betting lines or just trying to figure out who to root for, keep an eye on the injury report. This series has been dictated by who is actually on the floor. When Mitchell is healthy, Cleveland is a different beast. Their offensive rating jumps significantly because he demands so much gravity.
Chicago's path to winning is through pace. They want to turn it into a track meet. They lead the season series right now because they forced Cleveland into 15 turnovers in their last meeting and turned those into 20 fast-break points.
Next Steps for the Savvy Fan:
- Watch the Mitchell/Garland Split: The Cavs are still figuring out the "my turn, your turn" rhythm. If they combine for 15+ assists, they usually win. If they combine for 50+ points but only 6 assists, they usually lose.
- Track Matas Buzelis: He’s the X-factor. If he continues to play with the efficiency he showed in December (9-for-15 shooting), Chicago’s ceiling is much higher than people think.
- The Glass Battle: Cleveland relies on Jarrett Allen to anchor the interior. If Vučević continues to pull him out to the perimeter, the Cavs’ defense collapses.
The next time these two meet, expect a lot of points and a lot of complaining to the refs. It’s just the nature of the beast when it's Cleveland and Chicago.