 On the recommendation of Terry Cooper, now Southampton's chief scout, Dryden moved to Southampton on 6 August 1996 for £150,000.He made his debut on 18 August 1996 at home to Chelsea and successfully marked Gianluca Vialli out of the game in a 0–0 draw.Although he featured regularly in the first team under manager Graeme Souness in 1996–97 (making 29 league appearances), the remainder of his time at The Dell was difficult as Southampton had 5 managers during the course of his 5 seasons with the club.