Andy Rolland was born in Lumphinnans, Fife on 12th November 1942.
He became known as the Tommy Gemmell of the Second Division because he was an attacking full-back with a rocket shot and came to Dundee United's attention following his performance at East End Park in the match between a Fife Select and Sunderland for the Michael Colliery Disaster Fund, and was transferred three days later on 28th September 1967. He went on to make Dundee United's top ten appearances list with 326 League appearances for the club over an eleven year period.
Andy had been injured in the lead up to the 1974 Scottish Cup Final and although he was fit by the time of the final, he lost his full-back place to none other than former Pars striker Pat Gardner who had played well in the semi-final win.
When he was in America in 1978, he found himself marking George Best.Not only did he win the Man of the Match, but he went on to be transferred to Best's team the Los Angeles Aztecs!
He signed for Dunfermline on 24th August 1978, just a few months short of his 36th birthday.
Dunfermline, meantime, were going through a difficult time. Having finished third for the second year in a row and thus failing to escape from the Second Division, the Pars were suddenly in crisis when manager Harry Melrose was taken into hospital quite seriously ill. The Club decided to appoint a Coach and initially Pat Stanton was going to take the job but decided to move to Aberdeen instead.
This cleared the way for Rolland to take the job on.It was a big responsibility for someone with no previous experience, but he was an instant success.By the end of October 1978, Dunfermline were top of the Second Division and had gone ten games undefeated under Rolland's guidance.This had given them exactly the kind of start they needed to get into the promotion fight and by the time the season was nearing its climax Dunfermline were scrapping it out with Falkirk to decide the second promotion place.
It all came down to the last game of the season against the Bairns.Falkirk took the lead early in the second half but Dunfermline were awarded a penalty.With nobody bearing to watch, Rolland coolly stepped up to score the equaliser for the one point that would secure promotion.
Although nearing his 37th birthday, Andy accepted a short-term contract for the following season but after 45 appearances for the Pars shocked East End Park on 31st October 1979 by leaving after a fall-out over payments to join Cowdenbeath for the third time, this time as manager. Spurred on by their new boss, Cowdenbeath challenged for promotion.Unbelievably, they required one point on the last day of the season and were awarded a penalty. This time Andy missed (his first penalty miss for six years), Cowdenbeath did not get promotion and remained there until Rolland resigned in 1982.
At the age of 40, he was re-instated to the junior ranks with Leven Royals and played for several years in the Fife Junior League.