Hamilton Accies legend Alex Neil experienced plenty of highs during his time at New Douglas Park, from lifting the old First Division title to winning the Premiership play-off final that memorable day at Easter Road in 2014.
The Challenge Cup, or SPFL Trust Trophy as it is now known, was a thorn in his side, however, as he ended up on the losing team twice under boss Billy Reid in 2005 and 2012.
This weekend, Neil’s old club are aiming to put those demons to rest by lifting the trophy for the first time since their 1992 triumph over Morton at Love Street, where a Chris Hillcoat effort and Gary Clark double delivered a 3-2 win.
And Neil, who is now manager at English Championship side Stoke City alongside fellow former Accies boss Martin Canning, is backing Hamilton to go one better than he managed as a player when they face Raith Rovers at the Falkirk Stadium on Sunday.
He said: “I think it is going to be a tough match.
“I think it will come down to who holds their nerve and I think, with the momentum and the form Hamilton have been in of late, they have a good chance.
“I think they will see it as a welcome distraction from the league and I fancy them to go on and win the game.
“It has been a difficult season for them overall [at the bottom end of the Championship table], but they have been absolutely flying of late.
“Since the turn of the year, they have done a good bit of recruitment in terms of getting bodies in to help them [including Tom Sparrow from Stoke] and I think they have been one of the form teams in the league recently with some of the results they have picked up.
“If they win the cup, they would take huge belief and confidence in terms of how good they are as a team and, hopefully, that can set them up for the rest of the season in the league.”
Neil lost the 2005 final in the Challenge Cup 2-1 to St Mirren and more pain followed in 2012 when a 1-0 win for Falkirk, courtesy of a Darren Dods goal after just two minutes, proved decisive.
The 41-year-old knows he can’t offer any advice on what it takes to win the competition itself, but his success as a manager in England, where he took Norwich City to the Premier League in 2015/16 and Sunderland to the Championship in 2022, both via the play-offs, means he knows exactly what it takes to triumph in pressure games.
Recalling his cup finals with Accies, he said: “That first final in 2005, my memories of it are we changed shape for it and Billy [Reid] put me to right wing back, where I don’t think I’d ever played before, so that was quite bizarre.
“But in terms of the game itself, I remember St Mirren scored late on through John Sutton, so that was disappointing. We had a good team that season and we always fancied our chances of winning games.
“I don’t remember much about the 2012 final. We lost an early goal. I think the two James’ [McCarthy and McArthur] had just left the club and it was disappointing we didn’t win.
“So the closest I can get to the experience of winning one of these types of games is in the play-off finals in England.
“When I’ve won those, it feels like all the hard work is worthwhile and it feels great. When you lose a final, it just spurs you on because you don’t want to sample that pain again, feeling like you’ve let people down.
“When I was at Hamilton, we had a really successful spell for a number of years. We had two promotions, cup finals, quarter-finals of the Scottish Cup and things like that.
“You always look forward to the big games and Sunday is a really big one for the club.
"We've got Tom Sparrow up there on loan so I am in regular contact with the club, plus Ronnie MacDonald and Colin McGowan [board members and ex-chief executives] are really close friends of mine. I speak to them on a regular basis about the club."
Neil had intended on cheering Accies on in person in Falkirk, but he has revealed his wife has scuppered his hopes of attending.
He admitted: “My initial plan was to come up to the game but, unfortunately, my wife has actually booked a trip to London without my knowledge!
“So I’ll need to keep my eye on the result and for more reasons than one.
“I want young Tom Sparrow to do well and I want Hamilton to do well because I’ve still got a lot of friends there.
“Martin [Canning] is going to the game, I believe, because I had spoken to him about heading up there, so he will keep my up-to-date.
“I’ll certainly be rooting for them.”