Linlithgow, Lothian born inside forward Jimmy Blessington began his playing career with several Edinburgh sides, namely Harp Athletic in 1889, Hibernian (as an amateur) and Leith Hibernians in 1890, Leith Athletic in 1891 spending time at St Bernard’s in 1892 before moving to Glasgow to join Glasgow Celtic in August 1892. He made his debut in the Glasgow Cup at Pollakshaws Athletic in September 1892, and scored 9 goals in his debut season as The Bhoys claimed their first League Championship and were runners-up in the Scottish Cup, losing the Final to Queen’s Park in a replay at Ibrox.
He spent six seasons at Celtic Park, winning three Scottish League Championships between 1893 and 1895 and also appeared in two Scottish Cup Finals. Blessington was capped four times by Scotland between 1894 and 1896 during his time with Celtic. He also made five appearances for the Scottish League representative side, scoring once.
Having scored 38 goals in 99 appearances for Celtic, he moved to Preston North End in February 1898, making his Football League debut against Stoke at the beginning of March, but he only played 15 games, scoring once, before moving to Derby County in 1899. He only managed 2 appearances for The Rams, however, and joined Southern League Bristol City in 1900, followed by a move to Luton Town in 1901, where he stayed two seasons.
He returned to Football League action playing for Leicester Fosse between 1903 and 1909, acting as player-manager for the last two years, becoming that club’s first manager in 1907. He was in charge until April 1909 for a total of 91 games. Once retired from playing, Blessington then moved to Ireland, where he helped to coach Belfast Celtic.