Hope springs eternal for the St Mirren defender as he prepares to take on his former club Aberdeen in this year's quarter-finals on Tuesday, but he has never been closer to lifting the trophy than he was in May 2010.
The Paisley side were locked at 0-0 against a nine-man Rangers side only to be undone on the counter-attack and hand the trophy to the Ibrox club in the most agonising manner imaginable. Success in the cup competitions has become something of a crusade for the Pittodrie club in recent seasons, but few will have greater incentive to prevail in midweek than Mair.
"It was the worst day of my football career," Mair said. "It was a highlight to get to a final, but to lose after playing so well and after they had gone down to nine men was just devastating. At 11 v 11 we were playing brilliantly, creating chances and deserving to win. Then they went down to 10 and thought, 'we've got a right chance here'. At nine men we thought, 'we've done this'. But Rangers just sat in, kept to their back four and we couldn't break them down. These things happen and unfortunately it did to me."
The images of the moment remain etched upon Mair's memory. David Weir read Craig Dargo's dummy from his pass, the ball was funnelled out to Steven Naismith and seconds later Kenny Miller's header was in the net.
"It's silly now looking back on it," Mair said. "We thought, 'we have to win it, we have to win it'. Yet we could have played it properly and gone for extra-time against nine men. It's easy in hindsight. We should have taken a deep breath and thought about what was happening. I've thought about it loads and loads of times in my career. There aren't many of us left from that time but unfortunately I am one. To get St Mirren to a final again would maybe repay the fans a bit and to lift that trophy would be something special."
St Mirren are unbeaten in their last seven visits to Pittodrie, but this isn't the tie Mair would have chosen. Although you could slide a cigarette paper between the abilities of every team in the SPL outwith Celtic, Aberdeen are packed with experienced players such as Russell Anderson – who left the club shortly after Mair arrived – and his old Dundee pal Gavin Rae.
Having said that, Mair was part of the Aberdeen squad which lost a Scottish Cup semi-final to Queen of the South so he knows all about the pressure that can build on the Pittodrie side as a result of the 17-year trophy drought which has followed their 1995 Coca-Cola Cup win. The St Mirren defence will have to tighten up if they are to have any success, having been criticised by manager Danny Lennon after the five-goal rout by Celtic.
"It's probably one of the two ties we didn't want – Celtic away and Aberdeen away," said Mair. "But I don't see why we can't get back to a final. Outside of Celtic there's not much between the teams in the league. It's just getting that consistency right, like Aberdeen have managed recently.
"Everyone connected to Aberdeen is desperate to get to cup finals when you think that Gretna, Dundee, QOS and other so-called smaller clubs get there," he added. "I hope that pressure affects Aberdeen. But they have players on a high, are unbeaten in 11 games, consistent and hard to beat.
"They seem to have a great mix of Gary Naysmith, Mark Reynolds, Russell Anderson and Gavin Rae then the youngsters of Ryan Fraser and Ryan Jack who's injured and will be a miss for them. The experienced heads keep them right."
