Sam Deering started his career as a youth team player with both Chelsea and Charlton Athletic before linking up with Oxford United's youth setup. He was promoted to the U's first team in 2008 and went on to make his first team debut against Weymouth. Unfortunately Sam broke his leg soon after but joined Newport County on a one month loan on his return to action. He returned to action with Oxford and was an integral part in helping the U's find their way back into the Football League.
In February 2011 he was loaned to Barnet for the remainder of the 2010-11 campaign and helped to maintain the club's Football League status. He signed permanently with the Bees and went on to make 48 appearances in all competitions last season scoring five goals before departing the club for pastures new. He signed a two year contract here at Cheltenham Town in the summer of 2012 following his departure from Underhill.