Career
Leicester City
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 for a potential "six figure sum". Where he joined Leicester City"s development system, primarily playing for the under-18 and under-21 teams.
= Mansfield Town (loan) On 21 February 2014, Cain joined League Two side Mansfield Town on an initial one-month loan deal.
Cain made his debut for Mansfield as a second-half substitute, replacing Chris Clements in the 67th minute of their 1–4 defeat to Bury. = Return to Leicester On 26 August 2014, Cain made his Leicester City debut, along with fellow academy graduates, Ryan Watson and James Pearson, in the 0–1 defeat to Shrewsbury Town in the League Cup.
= Walsall (loan) On 20 October 2014, Cain joined League One side Walsall on a one-month loan. Cain made his debut in the 1–0 defeat away to Crawley Town on 21 October.
On 17 November 2014, the loan was extended for a further month.
Cain scored his first goal on 9 December 2014, in the 80th minute of the Football League Trophy fixture against Tranmere Rovers, to make it 2–2, sending the game to penalties, Walsall eventually winning 5–4. After making twelve appearances in all competitions for the Saddlers, Cain"s loan spell was extended by a month on 22 December 2014. On 10 January 2015, Cain scored the first league goal of his professional career, in the 1–4 defeat to Scunthorpe United.
Cain"s loan spell was extended until the end of the season on 20 January 2015.
