Josh Keeley and Jamie Donley have one more opportunity to pull on a Leyton Orient shirt following their play-off heroics on Wednesday evening. Travelling to Stockport County for the second leg of their League One play-off semi-final, the O's triumphed on penalties to set up a Wembley final date.
Playing out a 1-1 draw on the night and surviving a couple of scares with the hosts having good opportunities to win at the end of normal time and extra time, Orient prevailed 4-1 on penalties. Keeley had a big role to play in the shootout after saving Jack Diamond's penalty to give his loan club the advantage.
Tottenham duo Keeley and Donley have been instrumental in Leyton Orient's rise up the table to the play-off positions and they now have the opportunity to cap off their loan moves by guiding Richie Wellens' side to the Championship. Spurs boss Ange Postecoglou was watching the game on Wednesday evening and he was "super pleased" to see both Tottenham youngsters carry on their loan success.
"Yeah, I watched the game last night, it was a cracking game and super pleased for both of them," he told football.london in his pre-match press conference ahead of the Aston Villa game. "You know, when players go on loan, obviously the key for it is for them to get match minutes and development, I think both of those guys have, but it's even better if they're part of something that could be special for them in terms of success.
"I think that helps as well in terms of their own self-belief and and being part of something successful. So yeah, super pleased with them, it'll be a great occasion and hopefully they get through."
Asked if both can have a long-term future at Tottenham, he replied: "I think with all these things, they're for the off-season when guys come back. Right now our focus is fairly on what's happening in the next two weeks."
Opportunities are always there for the club's youngsters in pre-season, with Donley someone who featured in a handful of games last summer. Keeley, on the other hand, is still waiting to make an appearance under Postecoglou and Spurs fans are hopeful that will be sooner rather than later.
What makes things tricky for the Irishman is that he has Guglielmo Vicario, Antonin Kinsky, Brandon Austin, Fraser Forster and Alfie Whiteman ahead of him in the pecking order right now. With only one position up for grabs and some excellent options ahead of him, it's hard to see where his chance in goal will come from.
There may be an opportunity for him this summer, especially as there looks set to be some changes in the goalkeeping department ahead of the 2025/26 campaign. As things stand right now, both Forster and Whiteman will depart Tottenham Hotspur Stadium at the end of June unless there is a change to their contract situation.
The duo are now in the final two months of their respective contracts and it would appear their futures lie elsewhere. That in turn could open the door for Keeley this summer when it comes to his Tottenham career, although another loan move, perhaps in the Championship this time, could be the next step in his development given he is only 21 years of age.
With 16 clean sheets in 36 League One games, a goal in the FA Cup and penalty shootout heroics on three separate occasions, it has been an incredible season for Keeley, who was handed his first senior Republic of Ireland international call on Wednesday. It could be set to get even better if Leyton Orient are to secure promotion to the Championship at Wembley later this month.