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Rothesay, Isle of Bute born right half Jimmy Haig began his football career with Rothesay Royal Victoria, from where he was signed by Scottish League club St Mirren in 1897. From there he was signed by First Division club Derby County in 1898 and made his Football League debut at Preston North End that December, making two further appearances for The Rams in March and April before returning to Scotland to join Kilbarchan later in 1899.
Haig returned to Football League action in 1900 when he signed for Second Division club Chesterfield Town, making his debut in  home win against Newton Heath (now Manchester United) three days before Christmas, and he immediately became a regular for The Spireites, missing only two matches in the following three seasons when he was an ever present in 1902-03 as Chesterfield finished sixth in the division. He was again an ever present in 1906-07 but played his last match of 244 appearances for Chesterfield in January 1907, scoring twice for the club, one a penalty against Burton United in October 1903, his only other strike coming in a 2-0 win over Barnsley in September 1905.
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