Oakes first club was Leicester City where he stayed from 1998-2002 , despite their arrival in the Premiership it was decided to loan Stefan out to Crewe Alexandra , he then signed for Walsall in July 2003 on a free transfer.He could not make an impact there though and less than a year later made the move to Notts County where after an impressive season Wycombe boss John Gorman moved in and signed the midfielder on a two year deal