Born at Higham Ferrers, Northamptonshire in 1879.
Charles served an apprenticeship as a harness maker before starting his football career with Rushden, of the English Midland League, with whom he played between 1898-1900. A year later he spent a season with Kettering Town who had recently joined the Southern League. The following two years saw him play for Leicester Fosse and Wellinborough, before joining Southampton in 1904.
He had a successful time at the Dell, a regular first team player, and being influential in F.A. Cup matches. This brought him to the attention of Dundee F.C., and with the encouragement of Bert Dainty, an ex team-mate, he made the move to Dens Park in 1905. Although this nearly didn’t happen when an English club made an offer at the last moment.
Charlie made his debut on September 2nd 1905, in a 3-1 win against Morton, and soon settled into the first team line-up. He lodged with his club captain, Jack Fraser, in Union Street.
When Hearts played Dundee in October 1906, their manager , Mr Waugh, commented ruefully to his Dundee counterpart that they had had the opportunity of signing Webb, but “he was unknown to them” and so “were hesitant to engage him, a hesitancy they had not ceased to regret.”
1907 was trying for the player, Charlie was out through injury, to both his knee and leg , and his father died. It was rumoured that Dundee wouldn’t offer him a contract for the following season, even though he keen to sign on, as he felt he had recovered and was now fully fit.
1907-08 proved to be his final year with the club, and he was transferred to Manchester City at the end of the season.
Dens Park proved to be where he spent the longest spell of his career, as after a year with City, in as he was released, and joined Airdrie for a short spell.
During World War 1, Charles enlisted as a Saddler. After retiring from football he worked for several leather firms as a sales representative. He also continued with his other sporting passion, cricket, and payed for Higham Ferrars Cricket Club.
Charles died at home in Rushden, aged 59, in January 1939, and he is buried in Rushden Cemetery