Jameson represented Shamrock Rovers, Dundalk (loan), St. Patricks Athletic and Bohemians during his career. He is known around Dalymount Park as "The Great Man". He was inducted into the Bohemian F.C. Hall of Fame in November 2007.
Jameson played his schoolboy football at Lourdes Celtic and Cherry Orchard before moving into League of Ireland football with Shamrock Rovers in 1975.
He made a scoring debut on October 21, 1975 in a League Cup tie while in the previous month on the 11th of September he scored against Japan in a 3-2 win in Tokyo. He struggled, however, to gain regular first team football under John Giles and after only 5 appearances he moved to St Patricks Athletic in 1978 where he began to establish himself as a player of some class. He spent 3 seasons at Pats, reaching a FAI Cup Final in 1980 (losing to Waterford) before he joined Billy Young's Bohemians in 1981.
He spent 9 years at Dalymount Park until his retirement in 1990. Jackie would end up as Bohemian's top league scorer in 5 of those seasons. He was runner up in the FAI Cup in 1982 and 1983 and runner up in the League of Ireland in 1984 and 1985. He was never capped at full international level either. However, he was on the League of Ireland Representative XI and the Irish Olympic team. He played 303 competitive matches for Bohs after making his debut against Shelbourne on August 30, 1981 with his last game on January 28, 1990 against UCD. Scored once in six European appearances.
Later played non league with Newbridge Town F.C..
Jameson died in 2002. He is still a legend amongst the Bohs fans and many songs and flags have been created in honour of him.