Leith, Edinburgh born left half Tom Cleghorn began his football career with Darlington St Augustine’s in 1888 and played for Darlington in 1890 before joining hometown Scottish League club, Leith Athletic in 1892. He joined First Division Blackburn Rovers in the summer of 1894 making his Football League debut against Stoke that September and made a name for himself as a tough tackling left half. “A great little player who never knew when he was beaten. He worked like a demon, tackled effectively and headed the ball with wonderful skill. His value was enhanced by the judgement he displayed in feeding the forwards. On many occasions Cleghorn roused crowds to a frenzy of enthusiasm.”
After 3 goals in 48 appearances during his two years with Blackburn, he joined Second Division Liverpool in March 1896 where he played 70 games over the next three seasons scoring once in a 4-3 FA Cup Second Round victory over Burton Swifts in January 1897. His first contribution for The Reds was to play the final three games and then four Test matches that ensured Liverpool’s promotion as Second Division Champions. In his first full season he played in 5 FA Cup ties, scoring once, as Liverpool reached the FA Cup semi final for the first time in their history, losing 3-0 to eventual winners Aston Villa at Bramall Lane. He was an ever present in 1897-98 but played only 6 games in the 1898-99 season as Liverpool finished runners up in the League Championship.
In the 1899 close season he signed for Portsmouth where he later played under Frank Brettell and won the Western League and the Southern League with Portsmouth in 1901-02, making 66 appearances for Pompey. When, in 1903, Brettell took over as manager of Plymouth Argyle, he recommended Cleghorn for the position of team trainer and noted that he could also serve as a reserve half back. This he did for three seasons, playing 5 first team games for Plymouth between February 1904 and February 1905 in addition to his coaching duties, retiring from playing in 1906. As a player he was known as dour, experienced and everlasting; as a coach, clever, conscientious and well esteemed by all.