The youngsters needed a win to advance to the Round of 32 following a positive league phase campaign. 

Finn Leddie and Kerr Waddell strikes were each cancelled out by Dean Cleland inside the opening 25 minutes, before Owen Calder put Hibs ahead shortly before half-time.

Jamie McMurdo thought he had secured passage into the next stage with a 79th minute goal, only for League One Montrose to strike twice in the final 10 minutes. 

After the final whistle Darren McGregor admitted his disappointment and frustration.

He said: I’m very disappointed,” McGregor commented. “I think to do so well in parts of the game and to get ourselves in a position whereby we’re leading a League One team by two goals with ten minutes to go and then to lose their goals, draw, get knocked out, is very disappointing. 

“I can tell the lads are disappointed as well, but you come all the way up here, you work so hard – and we talk about momentum in football, and we know this is the start of a really tough couple of weeks, and we wanted to get it off to the right manner. Unfortunately we never done that. 

A dubious penalty decision in the final minute of regular time ended Hibs hopes of progressing.

McGregor added:”I think referees have a tough job. I totally understand that. I never really enjoy giving referees a hard time because I understand it’s a very difficult job, but I don’t think it’s a penalty.

“I think there’s a little bit of contact there. Nobody’s claiming for it and I personally don’t understand why it has been given. It doesn’t alter the lad’s run at all and, again, nobody claims for it. It seems to come out of the blue, which is very disappointing.

“But again, even before that when we take the lead, I think we commit eight bodies forward and leave two-v-two at the back having just scored to make it 4-2. I’m now saying to the lads, you need to manage the game better. You need to be left with one defender spare at the back in transition and we failed to do that and we paid the price.”

McGregor is now keen to move onto Friday’s U18s match – which sees Hibs take on Partick Thistle in the Scottish Youth Cup at Petershill Park. 

“We’ll have Partick Thistle on Friday, so that’s a Scottish Youth Cup game to look forward to. We’ll analyse this game on Wednesday and after Wednesday, we’ll just draw a line under tonight’s match. This is part of their learning because it would have been great to progress.

“I think there’s only going to be two B Teams now progressing into the next round. We should have been one of them. But we aren’t, so we need to reflect on that, we need to learn from it and then we’ll just push forward into the coming weeks.”