 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.Oakes played once for the "Silkmen", in a 2–0 FA Cup defeat to Rochdale, where he reportedly played with a broken finger.After the season finished he moved on to Northern Premier League side Winsford United.