After a spell in junior football, he returned to Central Park in 1964 and remained for three seasons, before a £10,000 move to Dundee United in 1967.
Rolland played at Tannadice for eleven seasons, picking up a Scottish Cup runners-up medal and making some 429 competitive appearances, putting him in the top ten for United players.
In summer 1978, Rolland moved to the US to play in the North American Soccer League, featuring for Fort Lauderdale Strikers and Los Angeles Aztecs, the latter involving a swap deal for George Best.
Rolland returned to Scotland after the summer and signed for Dunfermline, where he scored the all important penalty in the last game of the 1978–79 season v Falkirk to secure promotion for The Pars as runners up to Berwick Rangers Midway through 1980–81, Rolland returned to Cowdenbeath for a third spell, becoming player/manager shortly afterwards.
During that season, Rolland missed the all-important penalty in a match which denied Cowden promotion.