Cutler originally joined Swansea on loan from Stoke in the 2002/03 season and played a major role in retaining the club's league status. After spending the following season battling for his place at the Britannia Stadium, Cutler angered Kenny Jackett by turning down a move at the 11th hour, to join League One outfit Stockport. Cutler had originally agreed terms to sign for the Swans, before demanding an increase in his basic wage at the last minute, angering both Jackett and Swansea supporters.
However, after a disappointing season of relegation with Stockport, Cutler has been told that he is surplus to requirements at Edgeley Park and can leave on a free transfer. Meanwhile, Swansea, who eventually signed impressive keeper Willy Gueret instead, will take Stockport's place in League One next season.