When Bulls' Caleb Wilson Will Battle Dybantsa, Peterson, and Boozer This Season

During the NBA Draft Combine, Caleb Wilson aleady sounded destined to for the Chicago Bulls.

The forward was asked countless times about his on-court mentality, which appeared ruthless during his days at UNC. He was an all-gas, no-brakes kind of player, making repeated hustle plays with his explosive athleticism. Wilson said he got this relentless drive from adopting a similar mentality to that of another Tar Heel turned Bull.

"I always find something to make it personal, honestly. Just like Michael Jordan. I try my best to find something to piss me off," Wilson told ESPN in May. "It’s hard for me to be friends with someone off the court and then try to be competitive on the court. I just can’t do it.”

It didn't take long for the Bulls to see this (familiar) philosophy at work. During Summer League play, Wilson sounded legitimately frustrated that he didn't get a chance to match up against each of the three players selected ahead of him. To be clear, the NBA scheduled the games, but two of the three decided to shut things down early.

"I feel like I’m different than all of them," Wilson said after he didn't get a chance to battle Utah's Darryn Peterson. "I can’t say they don’t enjoy basketball, but I enjoy basketball. I love this sh*t. I’m going to play as much as I can, as much as my team will let me."

Those are fighting words, and Wilson is now inching closer to getting his chance to back them up. The 2026-27 schedule was released on Thursday, and Wilson is now slated to play AJ Dybantsa, Peterson, and Cameron Boozer a combined eight times. The first battle will even come just four days into the regular season!

Below are the dates Caleb Wilson will almost certainly have circled on his calendar.

Caleb Wilson vs. AJ Dybantas

October 24, 2026 (Home)
November 20, 2026 (Home)
February 8, 2027 (Away)
March 31, 2027 (Away)

The Chicago Bulls' home opener will pit Caleb Wilson against No.1 overall pick AJ Dybantsa. The two will also face off in an NBA Cup game before they meet two more times throughout the regular season. In other words, we'll be seeing plenty of these two!

For what it's worth, Dybantsa and Wilson never faced off during their collegiate careers, so this really will be a highly anticipated showdown.

Caleb Wilson vs. Darryn Peterson

December 16, 2026 (Home)
January 12, 2027 (Away)

Caleb Wilson will first meet No. 2 overall pick Darryn Peterson in December 16 on his home court. With the Utah Jazz expected to push for the playoffs this season, it's unclear just how much offense they plan to run through Peterson early on this season. Regardless, he will be a fixture of what they're doing moving forward, and Wilson will want all the smoke from the jump.

We might not get many one-on-one moments between the two, but there will be plenty of motivation for both after Wilson's Summer League comments. Not to mention, these two did meet early in last year's college campaign. Wilson beat Peterson 87-74 with 24 points, 7 rebounds, 4 assists, and 4 steals. The Kansas guard has 22 points, 3 assists, and 2 steals.

Caleb Wilson vs. Cameron Boozer

March 13, 2027 (Home)
March 25, 2027 (Away)

Arguably the meeting that fans want to see most is the one they will have to wait the longest for.

Cameron Boozer and Caleb Wilson will not battle until the Spring of 2027. The two put on a show in their Las Vegas Summer League debut. Wilson made history with his 35 points on 12-21 shooting from the field. He even went 7-11 from deep, matching the total number of threes that he made in college.

Meanwhile, Boozer posted a well-rounded 23 points with 6 rebounds and 4 assists. A mature Grizzlies squad would go on to edge out Wilson 97-96. And I'm sure he took that personally!

Out of any of the three matchups, this will be the one where we see the two players go head-to-head the most. Boozer offers fantastic fundamentals and a physical build. Wilson offers tantalizing versatility and explosiveness. The clash of styles should make for a fascinating game any time they meet.

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