As a senior, he led one of the best high school teams in history and received national player of the year recognition.

Cunningham committed to playing college basketball for the Oklahoma State Cowboys, and was named a consensus first-team All-American and Big 12 Player of the Year after his freshman season with the team.

[4] Since his childhood, he competed for the Texas Titans on the Amateur Athletic Union circuit alongside future TCU player Mike Miles Jr..[5] Cunningham attended Bowie High School in Arlington.

[4][6] Cunningham averaged 15.2 points, 6.4 rebounds, and 3.0 assists per game, helping Bowie reach the District 6A Region I final.

He was named District 4-6A co-most valuable player (MVP) and earned Texas Association of Basketball Coaches All-Region honors.

[14] For his senior season at Montverde, he was joined by many more top recruits, including five-star forwards Scottie Barnes and Day'Ron Sharpe.

[22] Sources: In his college debut for Oklahoma State on November 25, 2020, Cunningham recorded 21 points and 10 rebounds in a 75–68 win over UT Arlington.

[24] On December 12, Cunningham made a game-winning three-pointer with 11 seconds remaining to help defeat Wichita State 67–64.

[27] Cunningham posted 25 points, eight rebounds, and five assists in an 83–74 upset win against top-seeded Baylor in the Big 12 tournament semifinals on March 12, 2021.

[37] He missed part of training camp, all of preseason, and five of Detroit's first six regular-season games due to an ankle injury.

[38] In his NBA debut on October 30, Cunningham had two points, two assists, and seven rebounds in 18 minutes in a 110–103 win over the Orlando Magic.

[38] On November 15, Cunningham became the youngest player in NBA history to tally at least 25 points, eight rebounds, and eight assists with five three-pointers in a game at 20 years, 51 days.

[41] On January 25, 2022, Cunningham recorded 34 points, eight rebounds, eight assists, four blocks, and two steals in a 110–105 loss to the Denver Nuggets, joining Michael Jordan as the only rookies in NBA history to post such a stat line.

He became one of only 10 NBA players to average 17 points, five assists, and five rebounds in their rookie season, joining Luka Dončić, Tyreke Evans, LeBron James, Steve Francis, Grant Hill, Michael Jordan, Magic Johnson, Alvan Adams, and Oscar Robertson, becoming the only player other than Magic Johnson on that list to not win Rookie of the Year.

[48] On October 28, 2022, Cunningham scored a career-high 35 points alongside nine rebounds and eight assists in a 132–116 loss to the Atlanta Hawks.

[57] In the following game two days later, the Pistons ended their losing streak with a 129–127 win over the Toronto Raptors, with Cunningham recording 30 points and 12 assists.

[58] On January 7 against the Denver Nuggets, Cunningham had three points before leaving midway through the second quarter with a strained left knee.

[60][61] On November 8, 2024, Cunningham put up a triple-double with 22 points, 11 rebounds, and 13 assists alongside a game-winning floater in a 122–121 win over the Atlanta Hawks.

[62] He recorded a triple-double in his third consecutive game, tying him with Grant Hill (April 11–14, 1997) as the longest such streak in Pistons franchise history.

It was his sixth career-triple double, surpassing Isiah Thomas for the most triple-doubles in Pistons franchise history.

[65][66] On December 16, he had his sixth triple-double of the season with 20 points, a career-high 18 assists and 11 rebounds in a 125–124 overtime win over the Miami Heat.