Previous clubs: Leicester City, Mansfield Town (loan), Walsall (loan), Blackpool (loan)
Cain started his career playing for Luton Town in their youth academy system after having a successful junior career with AFC Dunstable. He was signed by Leicester City at the age of 16. He joined Leicester City’s development system, primarily playing for the under-18 and under-21 teams.
In February 2014, Cain joined League Two side Mansfield Town on an initial one-month loan deal, making his debut as a second-half substitute against Bury. Having made his debut for Leicester in the League Cup, he joined League One side Walsall on an initial one-month loan in October 2014. After scoring against Tranmere Roves in the Football League Trophy, Cain’s stay with the Saddlers was extended to the end of the season.
However, he was released by the Foxes over the summer and joined Whitehawk in September, making his debut in the FA Cup 2nd Qualifying Round against Oxford City.