'I felt so sorry for Bobby Linn': Raith Rovers star Jack Hamilton recounts 2022 Arbroath play-off agony

Hamilton, 23, then on loan to Dick Campbell’s Red Lichties from Livingston, had helped unfancied Arbroath to a fantastic second place finish behind Kilmarnock in the Scottish Championship, earning them a two-legged play-off semi-final against Inverness Caledonian Thistle.

But Hamilton and his colleagues suffered the misery of losing 5-3 on penalties after two 0-0 draws against the Highlanders, with Arbroath legend Bobby Linn having his spot kick saved by Mark Ridgers before Kirk Broadfoot won it for the visitors in a Gayfield second leg which also saw Caley finishing with nine men after Danny Devine and Wallace Duffy were controversially sent off.

"That is definitely up there with the most painful experiences I've had in my football career,” Hamilton told the Fife Free Press. "That was obviously not nice to not get through to the final. To get beaten on penalties as well wasn't the best.

"So that and getting relegated with Hartlepool last season are definitely up there.

"I think Bobby Lynn took it very hard missing that penalty. What a player, he's probably been one of the best players I've ever played with. To be a club legend and not to score his penalty must have been hard for him, but he's a great lad and he was able to bounce back straight away.

"I absolutely loved it at Arbroath. The boys were absolutely amazing with me and the gaffer, Dick and Pink (Ian Campbell), all the coaching staff and the fans were brilliant. I felt really confident up there, playing most weeks and scoring goals.”

Hamilton, who netted 18 times for Arbroath in 35 games across two spells, also spent six years as a Livingston player while being loaned out to the Red Lichties and six other clubs. He is gutted that the Lions have been relegated from the Scottish Premiership under his old mentor David Martindale.

"Obviously I was sad to see that,” he added. "Davie has been there since I came through so hopefully he can guide them back up and I wish them all the best.”