Stratford began his career playing for the youth academy at Fulham in England, eventually graduating to their reserve side.
At West Virginia he would finish his career as the all-time leader in assists (27) and most matches played (85). During his college career Stratford also played for the Cape Cod Crusaders in the USL Premier Development League.
He was drafted by D.C. United with the 24th overall pick in the 2008 MLS Supplemental Draft on January 24, 2008. He made his debut as a sub against the Kansas City Wizards on 29 March 2008 in D.C.'s season opener and got his first start on 26 April 2008 in a 4-1 victory over Real Salt Lake.
Stratford was waived by D.C. United on August 15, 2008.
He joined Scottish side Inverness Caledonian Thistle, following a successful trial on July 23, 2009.
Stratford was released by Inverness Caledonian Thistle on May 6, 2010.
Following a successful trial period he signed a one year deal at Hereford United on 16 July. He left at the end of the season after finding first team opportunities rare.
Stratford signed for Scottish First Division side Hamilton Academical on August 31, 2011.