And, the last time the club headed into a final showdown at the national stadium he was still part of the playing squad. Now, just over six months later, as the Leith club return to Glasgow for this weekend’s Premier Sports Cup finale, the 33-year-old former defender will lead the team out as interim manager.
While the club’s search for a permanent replacement for Jack Ross, who was sacked last week, continues, with an appointment imminent, the decision was taken to lock in Gray as the man who will take charge for the latest tilt at silverware, offering the squad a degree of clarity during a spell of ongoing uncertainty.
Victory would see his already legendary status elevated to unheralded levels but having just joined the coaching team in the summer, he admits that the challenge is sizeable.
“It is certainly different [this time]. I’m not sleeping as much at the minute, which is different! It used to be a bit different when I was preparing for games as a player. I used to be able to take myself away or the missus would take the kids away for a while and I would be able to get a bit of peace and quiet but right now I don't switch off at all. She has been great because I’ve probably not been great to live with over the past few days but as much as it is a difficult situation, it is something that needs to be done and I have great support from Sammy [goalkeeping coach Craig Samson] and Eddie [May, Lead Coach of Emerging Talent] as well.
“It’s not a great situation for us as staff to be in because people have lost their job and that’s not a nice situation but our job is to get the players ready to win the cup final now we know that’s happening.
“I’ve never been in this position so I don’t know exactly how it’s going to be. All I can do is pass on my knowledge and experience from when you're captaining the club and things like that. I’ve also got a very experienced group of players in there, the likes of Paul [Hanlon], Lewey [Lewis Stevenson] and Daz [Darren McGregor], players that have been there and done it all before.”
Gray says the fact that he has run the gamut of emotions on cup duty with Hibs can validate his message to the squad as they prepare for the face-off with Celtic.
“I’ve lost as well. I lost to Ross County in the [2016 League Cup final] and then lost in the Scottish Cup final so it’s all about using these experiences.
“I know how good it can be and I also know how much it can hurt if you don’t get the right result.
“The majority of the players have been involved in cup finals so they know how that feels. The most important thing is they’re excited about it and not worrying about it. There are only two teams left in the cup so why can’t it be us? We’ve shown this season that we’re more than a match for anybody on our day.”