On his international debut at the 2012 NACAC Under-23 Championships in Athletics he won the bronze medal. Cunningham reached new heights in the 2014 season, clearing in March. This made him the third highest ranked American vaulter that year, behind Mark Hollis and Sam Kendricks. Having failed to record a height at the 2012 United States Olympic Trials and the 2013 USA Outdoor Track and Field Championships, he finally placed at the competition at the 2014 USA Indoor Championships, coming fourth and still competing without sponsor. At the Outdoor Championships he fell back to last place in twelfth.