In the first half of extra time during Leyton Orient’s dramatic FA Cup victory over Oldham Athletic on Saturday, Josh Keeley made a crucial intervention.
Kane Drummond raced through on goal and fired a right-footed shot towards the top corner which momentarily looked like giving Oldham the lead. Keeley charged off his line, spread his arms and blocked Drummond’s effort with his face. The ball stung his cheeks but the pain was worth it when Dan Agyei scored to secure a 2-1 victory for Orient and a third-round tie with Championship side Derby County.
It was a brave piece of goalkeeping from Keeley, who is on a season-long loan from Tottenham Hotspur, but nobody was talking about it afterwards because the 21-year-old produced another moment of magic earlier in the game — one which will go down in Orient and FA Cup folklore.
The east Londoners were seconds away from exiting the competition when Keeley strode into Oldham’s box for a free kick in stoppage time. The Republic of Ireland Under-21 international’s glancing header hit the back of the net and he wheeled away before sliding on his knees in front of the raucous home fans.
“It was mad,” Keeley tells The Athletic a few days later. “I always go up for corners with an open mind, and it makes the supporters cheer, but you don’t expect to score at any time.”
The header was the kind of deft flick one would usually associate with an experienced striker, rather than a young goalkeeper.
“I have never practised it before,” says Keeley. “A few of my friends after the game said, ‘You scored that because of Pro Clubs’ because I play upfront for our team on FIFA (the popular video game series by EA Sports which is now called FC). So that’s my explanation. Everyone is delighted we are into the next round. Financially, it’s brilliant for the club.”
Keeley grew up in Ireland and only became a goalkeeper after getting into trouble for “flying into tackles” all the time as an outfield player. He began his career with St Kevin’s Boys and had spells with Shelbourne and Belvedere before moving to St Patrick’s Athletic. Keeley started training with the St Patrick’s first team when he was 17 and forged a close bond with the goalkeeping coach Pat Jennings Jr, the son of the legendary Spurs goalkeeper.
“He had a lot of contacts at Tottenham and told them, ‘I have a goalkeeper back in Ireland who I think is better than what you have,’ Keeley says. “I went over for a week’s training and came back on Thursday night because we had a league game the next day. On Friday morning, Tottenham rang St Pat’s and said, ‘We want to get him back this Saturday.’ So I flew over to London again two days after I got back.”
Keeley officially joined Tottenham in July 2022, less than a year after he made his Irish Premier Division debut as an 18-year-old in a 2-2 draw with Finn Harps. Although he has mostly been involved with the academy side during his time at Spurs, in 2023 he joined up with the first team on the club’s pre-season tour and worked with goalkeeping coach Rob Burch and No 1 Guglielmo Vicario.
“I always had a good laugh with Vicario,” Keeley says. “Ireland played Italy’s Under-21s and we conceded in the last minute. Vicario said the senior team were watching the game while they were on international duty so we had a chat about it when I came back. He’s been good and influential. You pick up a lot of things when you watch pros like him. Dean Brill, the academy goalkeeping coach, has been a huge factor for me too.”
During the 2023-24 campaign, Keeley made six appearances for Tottenham Under-21s as they won the Premier League 2 title. Keeley’s main focus during the second half of that season was helping Barnet’s push for promotion from the National League. He played 18 times for Barnet, who finished second in the division but lost 4-0 to Solihull Moors in the play-off semi-finals.
Keeley’s performances impressed everybody, so he was rewarded with a new three-year contract at Spurs and he jumped up two divisions to join Orient on loan. He made his first appearance in a Carabao Cup tie against Brentford and has slowly earned the trust of head coach Richie Wellens to start their last nine games in all competitions.
“Academy football is a big learning curve and a lot of the time you are working to improve your technical ability,” he says. “In senior football, a lot of players rely on winning games because they have got to feed their families and pay their mortgages. You learn how important it is to win.
“We have played well but haven’t got the results we wanted so it has been tough, but no loan or game is going to be easy, especially with the busy schedule coming up. I’m really enjoying my time here and working with (Wellens). Ever since I came in the door, he has been really positive. I had to wait my turn to get into the team but he was pushing me.”
Keeley is not the only player at Orient on loan from Spurs. Jamie Donley has made a positive impression too. The pair helped each other to settle and they will both return to Tottenham next summer more experienced and better equipped to break into Ange Postecoglou’s squad. Postecoglou praised Keeley, before Tottenham’s fixture against Bournemouth on Thursday evening, for his goal and breaking into the starting XI.
“You go into a loan club, especially as a young goalkeeper, and you have to earn the trust of the manager to end up being the No 1,” Postecoglou said. “The fact that he has and he’s doing well, it’s good. It’s what we want to see from our loan guys.”
Keeley has a close relationship with 19-year-old striker Will Lankshear and 17-year-old winger Mikey Moore, who have both featured in the Premier League and Europa League this season. They have set the example which he hopes to follow.
“I’m absolutely delighted for them because I know the quality they have,” he says. “It is massive for me as well to see young boys playing in the first team because I am out here on loan trying to get to that spot. My plan this season is to keep my performances up for Orient. My main focus is to win games and do my best for them. For the future, I’ve just signed a new deal (at Spurs) so if I can keep performing here you never know where it might take you.”
(Top photo: Pete Norton/Getty Images)