Youth Cunningham played with various local sides before attending the
Nike Academy, where he impressed enough to earn an academy contract at
Luton Town in 2010.
College & Semi Professional Following his release from Luton Town, Cunningham applied to various colleges in the United States, eventually been offered a scholarship to play
college soccer at NCAA Division II college
Roberts Wesleyan College in
New York. At Roberts Wesleyan, Cunningham made 76 appearances, scoring 30 goals and tallying 17 assists over four seasons and was twice named First Team NCCAA All-American, in 2012 and 2014. In the summer of 2014, Cunningham also appeared for
USL Premier Development League side
Southern California Seahorses.
Professional Cunningham signed his first professional contract In January 2016 with Australian
NPL Victoria 2 side
Northcote City FC. He went on to make 11 appearances for the club. Following a spell in Australia, Cunningham had a short stint with
Midland Premier League side
Quorn in the second half of 2016. Cunningham returned to the United States in 2017, joining
MASL indoor soccer side
Syracruse Silver Knights and later
Rochester Lancers. With Rochester in 2018, Cunningham scored 13 goals in 13 appearances. He made a single appearance for the indoor team in 2019, and scored 7 in 17 appearances in 2020. Rochester also operate an outdoor team who compete in the
NPSL, who Cunningham played with in 2019, scoring 4 goals in 10 regular season appearances. The 2020 season was cancelled due to the
COVID-19 pandemic. On 7 April 2021, Cunningham joined
USL Championship side
FC Tulsa following a successful trial. He made his debut for the club on 19 May 2021, appearing as a 74th-minute substitute during a 5–0 loss to
Atlanta United 2. On 20 September 2021, Cunningham joined
National Independent Soccer Association club
Stumptown AC on a loan deal. ==Personal==