Webb joined the "Saints" with a reputation as a "brilliant wing man (who) had a fine turn of speed, with his centres and long shots being particular features of his play".
During his one season at The Dell, Webb was in and out of the side making a total of 19 first-team appearances with five goals, with former England international Archie Turner competing with him for the outside-right berth.
[3] In the summer of 1905, Dundee made him an "irresistible offer"[1] to move to Dens Park along with his former Leicester and Southampton teammate Bert Dainty.
He remained at Maine Road until the end of the next season, when City were relegated, although he only made eleven appearances, as cover for George Dorsett.
After retiring from his football career, Webb managed a large bakery business in Rushden, back in Northamptonshire, close to where he was born.