[1] Roberts began his career as a trainee with Swansea City, turning professional in August 1998.
His first team debut came on 11 August 1998 when he was a late substitute for Jon Coates in the 1–1 draw at home to Norwich City in the League Cup.
His league debut came four days later in the 2–1 defeat away to Cambridge United, this time as a second-half substitute for Ryan Casey.
With Swansea in the midst of a financial crisis,[2] Roberts spent part of the 2001 pre-season on trial with Rotherham United[3] and moved to Wycombe Wanderers in October 2001 for a fee of £100,000.
[4] He remained with Wycombe until February 2004 when he returned to Swansea, initially on loan,[5] but a month later on a free transfer.