Having experienced years of disappointment in the competition as a fan of Dundee United, the lows finally gave way to a glorious high in 1994 when Bollan was part of the squad that ruined Rangers' treble hopes with a 1-0 win. He claims the victory left an indelible mark.
"That cup final was probably my favourite Scottish Cup memory as I suffered a few heartbreaks supporting Dundee United as a kid," reflected Bollan. "I was back and forth to Hampden many times with tears streaming down my cheeks so to be part of the squad that won their first Scottish Cup was an emotional moment for myself."
Six months after the wild scenes at Hampden Park, he signed for Rangers but his time at the club was blighted by injury. "I went there hoping to play regularly but hurt my knee in the final minute of an away Champions League tie against Borussia Dortmund," said Bollan, who will seek to end the hopes of his former club in this season's competition in his role as newly-appointed Airdrieonians manager. "I was out for the best part of two years. My time there was thoroughly enjoyable and I've absolutely no regrets about going."
Bollan shared a dressing room with Ally McCoist at Rangers and has watched with interest as his former team-mate has dealt with the considerable disruptions he has experienced since succeeding Walter Smith in 2011.
"The task Ally has had has been difficult but I take my hat off to him as he's managed to stick with the club through thick and thin," added Bollan, as he promoted tomorrow's tie among onlooking punters inside a William Hill shop in Airdrie. "You can see the progress made from last year and I'm sure he'll be looking to continue that. He's now on the other side of the fence but I'm sure he'll have the dressing room buzzing as he liked that as a player."
Bollan arrives at his new club with a point to prove. In his first senior post, he guided Livingston to consecutive league titles but was sacked earlier this year. He admits he is still reeling from the decision.
"I felt at the time I shouldn't have been out of a job and I'm still bitter about it. I feel I have nothing to prove to anyone after what I achieved at Livingston. I won two back-to-back Championships to get them back to the first division. I don't know what else I could have done as I achieved the task I was given in the shortest time possible. I still don't know why I was sacked."
Airdrieonians lie at the foot of League One having won just twice this season but Bollan is optimistic about what the future holds.
"I've wiped the slate clean and told the players they'll all get a chance to play. It's now up to them to prove they want to play a part in what I'm trying to do," he stated.
"When they are handed a jersey, it's theirs to lose and that's the way I work. We realise it'll be a gradual progression. We go into tomorrow's game as massive underdogs but there have been upsets in the cup in the past and there's nothing to say we can't cause one."