Edinburgh born left back Tom Wilkie joined hometown Scottish League club Heart of Midlothian in 1893 and after playing in four friendlies for the first eleven he made his competitive debut in a Scottish League victory over Dumbarton in April 1894, making 7 appearances for The Jambos in League and Cup.
He signed for Second Division Liverpool in the 1895 close season, making his Football League debut at Notts County that September. He scored his only League goal for Liverpool against Leicester Fosse in November, playing 23 matches during the campaign as Liverpool won the Second Division Championship. Wilkie established himself in the First Division in 1896-97, making 25 consecutive League appearances before being replaced by Billy Dunlop for the last seven matches of the season. However, Wilkie only played thirteen times over the next two seasons and his final game for the club came in a First Division fixture at Bury on 19th November 1898.
On the south coast of England Portsmouth Football Club had been formed to replace the defunct Royal Artillery Portsmouth club and was elected straight into the First Division of the Southern League in the 1899-1900 season. Wilkie became one of Pompey’s pioneers and had a successful career at the club, making 125 Southern League and FA Cup appearances for them between 1899 to 1904, helping them to win the 1901-02 Southern League Championship.