Oakes started his career with Barnton, but joined Macclesfield Town in the 1996–97 season as cover for regular goalkeeper Ryan Price as the club battled towards promotion into the Football League.
He played twenty games of the 1998–99 season, and his performances at Boothferry Park earned him a £465,000 move to Premier League side Derby County in June 1999.
[4] He immediately went out on loan with Port Vale but returned to Pride Park within three weeks having failed to make an appearance for Brian Horton's "Valiants".
Oakes joined Bolton Wanderers on loan at the start of the 2004–05 season as back-up to Jussi Jääskeläinen,[5] but only made the one appearance.
[8] Playing six games of the 2006–07 season, with only one appearances coming at the Liberty Stadium, he was not offered a new contract in the summer by new boss Roberto Martínez.