Dumbarton born left half John Tait “Jacky” Robertson began his football career in 1892 with junior club Poinfield and played for Sinclair Swifts in 1893 before joining Scottish League Morton in 1894. He moved to Everton in October 1895, not making his Football League debut until September 1897 when he played against Wolverhampton Wanderers at Goodison Park, but he became a regular member of the Everton line up during 1897-98 scoring once in 31 appearances before joining Southern League Southampton at the end of the season. Robertson made his debut for Scotland on 2nd April 1898 while at Everton, in a 3-1 home defeat to England in the Home Nations Championship at Celtic Park.
He spent a single season at Southampton in 1898-99, making 22 appearances as Southampton won the Southern League. His second Scotland cap came in a 2-1 defeat to England at Villa Park on 8th April 1899, while still at Southampton. Following that, he returned to Scotland to join Glasgow Rangers making a scoring debut in a 6-2 victory over Clyde in August 1899, and he won three consecutive Scottish League titles at Rangers in his first three seasons. All of his 14 remaining caps for Scotland came during his spell at Rangers, he scored 3 times for Scotland. He captained the Scots in his fourth match, as they beat England 4-1 at home on 7th April 1900 and also he played 6 times for The Scottish League between March 1900 and May 1905, scoring once, all but one of these appearances coming against The Football League.
He scored 23 goals in 129 games for Rangers before, in April 1905, Robertson was the first player to be signed by the newly formed Chelsea Football Club, and served as their player-manager in their first ever Football League season but continued to play as well. It was Robertson who scored Chelsea’s first competitive goal, in a 1-0 win at Blackpool on 9th September 1905 and he also played in their inaugural League fixture a week earlier in a 1-0 defeat at Stockport County. In his first season, he led the club to a third place finish in the Second Division, one place off promotion. Robertson then surprisingly resigned from the club (third in the table at the time) on 27th November 1906. Chelsea were promoted to the top flight at the end of that season under caretaker secretary-manager William Lewis, Robertson scored 4 goals in 39 appearances during his time at Stamford Bridge. In December 1906 Robertson became player-manager of Glossop, where he remained until summer 1909 scoring 10 goals in 49 appearances, when he became reserve team manager at Manchester United.