Wigan, Lancashire born goalkeeper Tom Pennington started his football career with Newtown in 1905, joining Shropshire club Combination club Whitchurch in 1906. Whitchurch both won The Combination Championship in 1907 and were runners up in the Welsh Cup Finals in 1906 and 1907. It’s not known if Pennington played in these Finals but it’s safe to assume he played in the 1907 Final, when Oswestry United beat them 2-0 at The Racecourse Ground, Wrexham.
Pennington moved to Southern League club Reading in 1907, staying a season at Elm Park before joining non league Saltney Town in 1908. In September 1909 he joined Second Division club Oldham Athletic, and made his Football League debut, and his only Football League appearance, in a 2-1 victory over Burnley at Turf Moor in October 1909. He was subsequently a trialist with Fulham in October 1912 but never made their first eleven.