Nick Montgomery needs no reminder of the Scottish Cup's significance to Hibs - they are all around him every day.
From immortalised images on training ground walls, to his assistant forever known as 'Sir' for his exploits in making the most storied afternoon in the club's history a reality, the famous old tournament is woven into the fabric of his day-to-day. It will come as no surprise to anyone who knows Gray that his fan-anointed knighthood does not sit entirely comfortably with a limelight-averse persona, but his presence and legacy are a constant symbol of where success in this competition can take you at Hibs.
Their quest to repeat the heroics of 2016 continues in Inverness on Saturday. Almost every team's run to a May date at Hampden comes via a perilous away venue that takes players out of their comfort zones, and a trip to the Highlands is exactly that. Despite a highly creditable performance in losing so narrowly - and perhaps undeservedly - to champions Celtic on Wednesday night, Hibs are not currently in the habit of grinding out victories when they need them.
Their winless Premiership run stretches back to December 9, and they just about navigated the previous round thanks to a solitary Christian Doidge goal away at League Two Forfar Athletic last month. But having been denied so frustratingly in the Viaplay Cup semi-final against Aberdeen at the tail end of 2023, Montgomery is adamant he and his players are determined to clear all hurdles between themselves and a return to the national stadium.
“I don’t need reminding of the success because David Gray is my assistant," Montgomery smiled. "Everyone calls him Sir David Gray, but he’s a really humble guy and probably doesn’t like that tag of everyone calling him that.
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"It’s something that David is really humble about, but we do have a laugh about it. I don’t think anyone can take that tag off him.
“You see photos around the training ground and in the gym with that moment when he scored the winning goal. You see the stories and the You Tube videos and it makes the hairs on the back of your neck stand up.
“So it’s great history and every cup competition is a great opportunity. I got to the semi-final in the last one and I thought we were unlucky not to make the Final.
“Probably best not to talk about VAR again, but we know that is something that are proud for a manager and a team and something to get your teeth into. Major semi-finals and Finals are something you really want to do.”
Montgomery has been haunted by the VAR spectre that hangs over every league match, and no more so than on Wednesday as Celtic were awarded a very, very late penalty to snatch three points away from Hibs. With the technology not in use at the Caledonian Stadium this weekend, can he rest a little easier knowing it won't be a factor in the tie, or could it be a case of 'be careful what you wish for'?
“Ask me afterwards!" replied Montgomery. "You definitely won’t see the screen there and the ref coming over to the side of the pitch. I think everyone agrees that sometimes the stoppages do stop the flow of the game, so there won't be stoppages and you have to be switched on and ready at all times.
“It’s always hard. Sometimes you are glad when you have it and sometimes when you don’t. It’ll be different and what you can’t do is play for offsides that are tight and you maybe not get.
“The mentality has to be a little bit different because you are relying on sometimes a blatant decision. You have to finish the action off. When you know there is VAR, you have to finish the action off.
But you know what you can’t do is anticipate anything and expect decisions to be overturned. Chopping and changing from VAR to not is definitely something you have to be cautious of.”
Montgomery was without Emiliano Marcondes against Celtic, but the on-loan Bournemouth playmaker could return for the journey north. Back in England, this may just have been the type of tie which would see Marcondes given a precautionary day off, but Montgomery suggested he will take no such chances against Championship opposition.
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"With cup shocks, I think it’s always a case of turning up unprepared and maybe underestimating the opposition," he said. "That’s something you can never do, it’s 11 v 11, it’s something you have to prepare for.
“The moment you don’t prepare properly you open yourself up to getting a result you don’t want or expect. I had a lot of success in cup competitions and getting to semi-finals and Play-off finals and stuff.
“There were one or two when we got knocked out. And I think if you look at a lot of the clubs in England with massive squads there’s also a lot of rotation that goes on in those games.
“We don’t have the luxury of being able to rotate a lot of players, we didn’t have up until two days ago. We still have players to come back.
“But you have to take the game seriously, it’s a cup competition with a lot of history for the club. I’ll do everything I can to prepare the team and get us through to the next round.
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