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Wolverton, Buckinghamshire born outside right Jimmy Frost began his football career with Wolverton LNWR, from where he joined Southern League club Northampton Town in May 1901. He spent six seasons with The Cobblers, scoring 14 goals in 174 appearances before being signed by Second Division club Chelsea for £350 in December 1906. Frost made his Football League debut against Clapton Orient the same month, scoring in a 2-1 victory and helping Chelsea to promotion at the season end as they finished runners up in the Second Division, however due to injury he only played 3 matches in the top flight that September before transferring to Southern League club West Ham United in January 1908 after 4 goals in 22 appearances for The Pensioners.
He scored 4 goals in 25 appearances for The Irons over the next 18 months before a transfer to Croydon Common in the 1909 close season, spending the 1909-10 campaign with The Commoners, scoring 4 goals in 29 appearances. He moved to Leyton in 1910 and was subsequently on the books at Clapton Orient without making their first eleven before his eventual retirement.
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