Background
Webb was born in Higham Ferrers, Northamptonshire and trained as a harness-maker.
Webb was born in Higham Ferrers, Northamptonshire and trained as a harness-maker.
Kettering finished their inaugural season in the Southern League 11th in the table.
After playing football for his village team, he joined Rushden of the Midland League in 1898. After two seasons with Rushden, in 1900 he moved to Kettering who had just been admitted to the Southern League as Midland League champions. His cup exploits brought him to the attention of Leicester Fosse of the Football League Second Division who signed him in May 1901.
Webb played in all but two of Leicester"s league and cup matches in the 1901-1902 season, scoring three goals.
lieutenant was at Filbert Street that he first teamed up with Bert Dainty, with whom he was later to play at Southampton (1904–1905) and (1905–1908). At the end of the season, he returned to the Southern League to join Wellingborough where he spent a season, followed by a year back at Kettering, before moving to the Southern League champions, Southampton, in May 1904 to replace Dick Evans who had been forced to retire through ill health and injuries.
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". He made his debut in the opening match of the 1904-1905 season, a 2–1 victory a Luton Town.
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.
In the summer of 1905, made him an "irresistible offer" to move to Dens Park along with his former Leicester and Southampton team-mate Bert Dainty. Webb remained with for three seasons, helping them to the runners-up position in the Scottish Football League in 1906-1907. In March 1908, he returned to England to join Manchester City of the Football League First Division, where he played the last eleven matches of the 1907-1908 season, scoring three goals to help City reach third in the table.
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.
In June 1909, Webb moved back to Scotland, where he played out his career with Airdrieonians. After retiring from his football career, Webb managed a large bakery business in Rushden, back in Northamptonshire, close to where he was born.