Started at Stoneyburn before spending seven years at Raith. Signed by manager Andy Dickson from Raith Rovers in March 1959 for £1,500, Jackie made 154 appearances for the Pars, scoring two goals (against Third Lanark and Stirling Albion).
Signed to strengthen a weak defence, Jackie played initially at left-back, but when centre-half Jimmy Stevenson broke his leg against Hibernian in December 1960, Jackie slotted into the vacancy and went on to make the position his own.
During the Cup Final against Celtic, Jackie picked up an injury which led to him being helped off just before half time. Surprising everyone by re-appearing after the interval, Jackie continued until 12 minutes before the final whistle, when he collapsed in agony. Stretchered off, Jackie amazingly re-appeared with just 4 minutes remaining to play out the remainder of the game on the wing. Jackie's determination and courage typified the never-say-die spirit of the Dunfermline team of 1961.
The injury incurred in the Final kept Williamson out of the replay. Still troubled by the Cup Final injury, Jackie decided to retire from the game at the end of season 1962/1963, and was rewarded by the club with a joint testimonial game (with Willie Cunningham)against Newcastle on 9th December 1963.
Jackie played in 7 of the 8 1961 cup games, missing only the replay against Celtic.