He played college football for the Vanderbilt Commodores and was selected in the second round of the 2017 NFL draft by the Houston Texans.

Cunningham made another huge, nationally-recognized play in the fourth quarter of Vanderbilt's game against Auburn, when he perfectly timed a leap over Auburn's left guard as the ball was snapped on a field goal attempt, allowing him to arrive in the backfield at the same time as the ball, which Cunningham then blocked the field goal to preserve Vanderbilt's chances to win with less than 2:00 minutes remaining in the contest.

A late interception by Auburn preserved the Tigers' victory, but Cunningham's leap was named Top Ten Play of the Day by ESPN.

[10] At the conclusion of the pre-draft process, Cunningham was projected to be a first or second round pick by NFL draft experts and scouts.

[19] Cunningham competed with Dylan Cole and Sio Moore for the starting left inside linebacker job with original starter Brian Cushing suspended for the first ten games of the season.

[20] He made his professional regular season debut during the Texans' season-opening 29–7 loss to the Jaguars and finished the game with five combined tackle and a pass deflection.

The following week, Cunningham earned his first career start and recorded six combined tackles as the Texans defeated the Cincinnati Bengals, 13–9.

[22] Cunningham entered training camp slated as a starting inside linebacker after Brian Cushing officially announced his retirement.

[24] In Week 2 against the Jaguars, Cunningham made a team high 10 tackles and sacked quarterback Gardner Minshew once as the Texans won 13–12.

[29] In Week 2 against the Baltimore Ravens, Cunningham recorded a team high 15 tackles (11 solo) and sacked Lamar Jackson once during the 33–16 loss.