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.
Rolland shifted from junior soccer to Central Park in 1964, where he stayed for three years before moving to Dundee United in 1967 for £10,000. He played at Tannadice for eleven seasons, securing a Scottish Cup runners-up finish and accumulating over 429 competitive games, placing him among the top players in United's history.