Andy Oakes joined Darlington ahead of the 2007/08 campaign following a year at Swansea City which was spent largely on the sidelines. Oakes started his career in the Northern Premier League playing for Winsford United.

Good performances however saw Hull City swoop and not long afterwards Premiership Derby County paid £465,000 to bring the keeper to Pride Park. The move earned Winsford a massive windfall of £115,000.

Oakes had to be patient but when he finally got him chance in the Premiership with Derby during the 2000/01 campaign he kept four clean sheets in six games between early February and early March. The clean sheets helped Derby stave off relegation but the following season the club was relegated. The 2002/03 and 2003/04 seasons saw Oakes make only a handful of appearances with Derby somewhat strapped for cash.

In August 2004 Sam Allardyce took Oakes to Bolton on loan as cover. Bolton eventually bought out the remainder of the keeper's contract but first team chances remained hard to come by. In March 2005 Oakes moved to Walsall where he made thirty-four appearances however he could not stop Walsall finishing bottom of League One at the end of the 2005/06 campaign. Oakes elected to stay in League One and joined Swansea ahead of the 2006/07 season but again first team chances were limited and after making just four starts in the league he joined Darlington.