He made his professional debut for Coventry City as a substitute on 13 April 2009 in a 0–0 Football League Championship draw with Charlton Athletic. During that game Cain had the chance to relegate Charlton Athletic as he went through one on one with the keeper after a bursting run and narrowly missed hitting the post. He signed a one-year professional contract with the "Sky Blues" in July 2009. He made his first start for the club on 12 August 2009 in a League Cup defeat to Hartlepool United after a successful pre season playing almost every minute of every single game for Coventry.
On 26 November 2009, Cain signed on a one-month loan with Conference Premier side Luton Town, making just one substitute appearance in a 0–0 draw at Chester City, although his only appearance for the club would later be wiped from the record books after Chester folded later in the season and their record was expunged.
On 19 February 2010, Cain joined Conference league leaders Oxford United on a one-month loan after scoring a hat-trick in the first 45 minutes against them in a mid season friendly match. He then had a trial with Port Vale in April 2010.
At the end of the 2009–10 season Coventry City told Cain he was surplus to requirements and he was subsequently released. He signed for Mansfield Town on 26 July 2010. Halfway through the season Cain established his place in the team, getting 12 goal assists in 10 games. This attracted the interest of Derby County, who made several enquiries to the club who at the time were not prepared to let him leave as they were a few games away from reaching the FA Trophy final at Wembley Stadium.
On 22 June 2011, Cain was picked up by Conference Premier side Tamworth. He was joined at the club the same day by former Coventry City teammate Liam Francis, who signed from Hednesford Town.
On 18 November 2011, Cain was loaned to AFC Telford United until 5 January 2012. In January 2012 his contract was cancelled by Tamworth and he joined Telford on a permanent basis. He was released by the club in May 2012.
In June 2012, Cain signed for CS Gaz Metan Mediaș after a successful trial period. Cain played in 3 trial games scoring 3 goals and getting 4 assists. This attracted big name teams in the Romanian Liga 1 such as CFR 1907 Cluj. Gaz Metan quickly decided to negotiate a contract and take Cain on pre season tour. During his first game for them he suffered a complete rupture of his right Achilles tendon, which would keep him out for the rest of the season, so he returned to England to receive treatment and recover. Because of this injury, he had to leave the club.
