Aberdeen might have gone back to the 80s in recent weeks, with more than 40,000 supporters booking their tickets for Sunday's League Cup final against Inverness Caledonian Thistle, while local retailers have produced pies and burgers nicknamed "The Sheep are on Fire". Yet Glass, who was the man of the match on the last occasion the Pittodrie side won a trophy - in November 1995 - is cautious about their prospects of ending that fallow period.
Perhaps that is a reflection of the fashion in which Glass' own cv is a tale of what might have been if he had been more fortunate with fitness and in moving to new challenges at the right time. As a teenager, nobody doubted his potential and the manner in which he orchestrated the convincing 2-0 defeat of Dundee in the 1995 Coca-Coca Cup final deserved better than the mountain bike which he received from the sponsors for being the game's star figure.
But despite going on to gain a solitary Scotland cap as a substitute against the Faroe Islands in 1998, shortly after completing a lucrative £650,000 transfer to Bobby Robson's Newcastle United, the midfielder struggled throughout his period in England. There were happier memories after he returned to Hibernian in 2003, where his consistent performances under Tony Mowbray helped the Leith side gain a UEFA Cup place by finishing third in the Scottish Premier League. But, to all intents and purposes, he was finished with top-class football at the age of 30. It would be easy for him to feel resentful about his travails.
However, now he is in the United States coaching the North Carolina Alliance squad and returning to Scotland fairly regularly and developing his mentoring skills. He will not be at Celtic Park for Sunday's final - his commitments in America preclude that possibility - but he will be there in spirit, cheering on Aberdeen and hoping they can rediscover their ability to glitter in these grand occasions.
"We used to have the attitude that we could beat anybody and I was one of the young guys in the 1995 side and I suppose I thought that these matches would come along on a regular basis, but football isn't like that for most teams," said Glass. "I don't believe the final result flattered us. We had a good blend, we still had a really big fan base and we thought that victory might be the impetus for us to challenge the Old Firm in the future. It didn't happen, of course. But I certainly wouldn't have guessed the club wouldn't win any silverware between then and now. It has been too long, to be honest, but they can take absolutely nothing for granted against Inverness."
On paper, Aberdeen are clear favourites, not least since Inverness have slumped to successive 5-0 losses. However, Glass does not read too much into the recent problems faced by the Highland side. "It might make them even more determined, because you hate losing that heavily and for it to happen twice in a row will have seriously fired them up," he added.
"You have to remember that they were down to nine men, yet still managed to beat Hearts to reach the final. You just can't discount Inverness on the back of two poor results."