He played college football at Middle Tennessee State and was signed by the St. Louis Rams as an undrafted free agent in 2013.

Cunningham attended Goodpasture Christian School in Madison, Tennessee, where he was a letterman in football, basketball, and track.

Also an standout track & field athlete, Cunningham was one of the state's top performers in the sprinting events.

[10] Cunningham was signed by the St. Louis Rams as an undrafted free agent in 2013 and made their 53-man roster.

[18] On September 10, 2017, in his Bears debut, Cunningham had one punt return for 23 yards in the 23–17 home loss to the Atlanta Falcons at Soldier Field.

[19] On October 9, against the Minnesota Vikings, he had a 38-yard touchdown reception from punter Pat O'Donnell on a trick play.

[26] After his playing career, Benny Cunningham alleged that the National Football League scripts its games and forces players to sign a non-disclosure agreement on the matter.