Andy made his professional debut in October 2001 for Stockport County and enjoyed three seasons there making 85 appearances. During his time there, he went out on loan to Macclesfield and played six times for the Moss Rose side.

November 2004 saw the winger sign for Sunderland after a trial there. He had to wait until January for his debut, though, coming on as a substitute for Marcus Stewart against Preston. He started the following week at QPR and scored on his full debut.

Sunderland were promoted to the Premiership that season and Andy found himself a regular in the team making fourteen appearances before Christmas playing against the likes of Liverpool, Manchester United, Arsenal and Chelsea among others.

In March of that season, he spent two months on loan at Leicester City playing ten games before returning back to the Stadium of Light to play in their final two matches against Fulham and Aston Villa.

The following season, 2006/07, he made another eight appearances back at Leicester City on loan before returning to Sunderland a second time.After Blackpool had beaten Yeovil in the play-off final, they strengthened their team by signing Andy on a free transfer in August and he went on to play twenty-one times in their first season back in the Championship.

Released at the end of that season, he joined up with Yeovil and was a regular in the first-team creating several goals with his dangerous crosses. He signed a two-year deal in the summer that will keep him at the club until the summer of 2011.

Season 2009/10 saw Andy as a regular fixture in the left midfield role and leading the way in terms of assists. He scored his first goal for the club against Brentford and added another in the win at Wycombe.