 In May 2000, against the advice for a longer contract offer given by youth coaches Paul Compton and Richard Hancox, Guttridge was only offered a three-month professional contract by Torquay manager Wes Saunders, even though Cambridge United had offered him a one-year deal and the chance to play Second Division football.Unsurprisingly, Guttridge left for Cambridge, managed by Roy McFarland, on a free transfer.He had to wait until the following spring for his Cambridge league debut, after playing twice in the Football League Trophy, but when it came he scored within two minutes in a vital 2–0 home win against Oldham Athletic.