Harry Gray arrives at Sheffield Wednesday with some excitement behind him. Alex Miller spoke to two men that know him better than most.
On January 24 this year, a football scout made his way up the stairs at the New York Stadium and settled into a seat to take in a League One relegation clash between Rotherham United and AFC Wimbledon.
The Millers were second-bottom and labouring and with every respect in the world, you can only imagine that to that point a glance down the list of clubs who had sent scouts to an S60 postcode to that point would make for fairly unremarkable reading. Theirs was an ultimately relegated squad soldered together with the parts of several managers preceding then-Rotherham boss and former Owl Matt Hamshaw. It wasn’t a hive of transfer market inquisitiveness.
So startling it was, then, that the scout in question had been sent by Barcelona. A few seats down sat a scout sent by AC Milan. Throughout a cold and dreary 1-1 draw that saw Marcus Browne’s late equaliser punch further air out of the Millers’ survival hopes, their eyes had been set on one man - or boy - in particular; Harry Gray.
Then-Rotherham United loanee Harry Gray. Picture: Jim Brailsfordplaceholder image
Then-Rotherham United loanee Harry Gray. Picture: Jim Brailsford
That Rotherham had landed the loan rights of the 17-year-old had been something of a coup. In a January transfer window in which Gray attracted motherload interest from League One clubs, Hamshaw’s existing relationship with his family was a guiding prospect, as was the New York’s proximity to Leeds - one that was also heavily considered when signing him over to Sheffield Wednesday for the coming season. The Owls appear to have landed one of the country’s most hotly-tipped young forwards.
He comes from a rich footballing dynasty of course. Dad Andy was an accomplished EFL and sometime Premier League forward who earned two caps for Scotland. Granddad Frank is a Leeds legend and also a Scotland international and there is no sycophancy in suggesting great uncle Eddie is one of the finest attacking players to grace the game.
Brother Archie was on the fringes of the conversation for a place in England’s World Cup squad this summer having made a £40m switch from their beloved Leeds United to Tottenham Hotspur in 2024. As recently as these last few months, when Hamshaw would check in with dad Andy to deliver a progress report, he’d be told that the brothers were in the back garden playing heated matches of one v one in the back garden.
“The people at Leeds think..”
“It always made me laugh,” Hamshaw chuckled to The Star. “You know what brothers are and like and his dad would just say, ‘Oh yeah he's just having a kick about with our Archie in the back garden. You've got somebody there who potentially could go on to do amazing things and you've got a Premier League football player. You can imagine them kicking lumps out of one another. They just love football.
“I think they'd be expecting that in the next couple of seasons Harry will be a regular starter for Leeds. The biggest compliment you can give him is that as good as his brother is and was at that age - he’s obviously now playing regular Premier League football - the people at Leeds think that Harry probably has a little bit more than Archie at his age. If he does as much as Archie has done then he's going to have some career.”
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A tally of three goals in his 20 Millers appearances doesn’t do his maiden loan spell justice. Arriving to the New York Stadium a little lighter in stature, he beefed up and rode the challenges of senior football, clearly appreciating the strides he needed to undertake from a goal-laden career playing above his age level with Leeds and England.
Arriving from the plush Premier League surroundings of Thorp Arch to Rotherham’s more primitive Roundwood Sports Complex, he cracked on and showed a confidence in personality perhaps unusual for a footballer who had turned 17 only three months earlier.
The Rotherham Advertiser’s Millers correspondent Paul Davis remembers the teenager pulling down the tracksuit bottoms of a senior pro in cheeky celebration of a rare Millers win at Leyton Orient - a prank known to teenagers as a ‘de-kegging’. Gray had scored and in the same hour, Orient boss Richie Wellens dedicated part of his post-match press conference to the talent of Gray alone.
All suggestions are that often there were passes or movements that his teammates simply didn’t register. The hope would be this time around that the likes of Barry Bannan can weedle out the same wavelength to turn that three-goal tally into something more substantial.
“It will have done him the world of good last year, albeit in what ended up being a struggling team,” Hamshaw said. “Seeing his reaction to things, knowing how much he cares and knowing how much he wants to win, it’s refreshing from a young player. He wasn’t big time and he wasn’t flashy, he mucked in. Harry just wants to play football all the time. Most fans might think that all footballers are like that, but trust me they're not.
“He wants to do extras, he wants to be out there, he wants to learn. He's just an unbelievable talent. The loan that he had last year will stand him in really good stead. I expected big things from him when I signed him, but I expect even bigger things now.”
“If Man City scored eight goals in a game, he'd get seven..”
The theme of Gray’s boyish love for football is a common one when speaking with people who have an insight into his development to date. Both brothers were among the scores of professional players to have enjoyed the benefit of Simon Clifford’s coaching in their early years and the Harrogate-based Futsal pioneer remains a trusted coach and confidant to the family to this day. He spent time coaching with Gray as recently as this summer.
Sheffield Wednesday's Harry Gray has worked with Simon Clifford since he was a boy. (Pic: Simon Clifford)placeholder image
Sheffield Wednesday's Harry Gray has worked with Simon Clifford since he was a boy. (Pic: Simon Clifford) | Simon Clifford
Clifford’s Socatots programme had and has bases across the country and it was at its Harrogate base that Harry rocked up as a four-year-old. Clifford, who spoke to The Star from an aeroplane that would take him to watch England’s World Cup semi-final in Atlanta, began working with him individually a couple of years later. He’d also coached Archie and counts Micah Richards, Oli McBurnie, Ryan Fraser and Gareth Bale among the many young players he’s worked with.
“He always stood out in the very beginning, he was probably different to any other kid that I'd seen at that age,” Clifford said. “Before he signed on with Leeds he had a couple of sampling years at Man City. He would have been five, six and pre-academy. We took him to a couple of tournaments in Europe and I think he got player the tournament twice. If Man City scored eight goals in a game, he'd get seven of them, and at one point I’m sure he was getting 300 goals a season.
“I've been working with him individually now for over a decade. Sometimes when you get to talk to the lads that you work with, I might say ‘Have you seen this movie, have you read this book, have you done this, have you done that?’ From a young age I realised that to engage Harry you just need to be on football and you need to know football inside out. That's the thing that gives him happiness and pleasure.
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Simon Clifford
“From a young age I don't think I've ever seen anyone so absolutely laser-focused on the game. That’s not just on Leeds or teams that he would generally take an interest in, he knows every player in every league. I don't think I'd ever come across a young person that was as in love with the game to the extent that he was and is. Even today, I was training Harry this summer just before he went off to Sheffield. When he was young he'd always have a football shirt on, this player or that player. Well he still does that now.
“Whatever player he's liking and watching videos of at that moment he gets that top. He was wearing a Lamine Yamal top last time I saw him. I think it's fabulous. He'll watch hours of footage of these players, he'll find out how to do this, he'll find out how to do that. He's as in love with the game as ever, no different. I only live around the corner from him and I’ve barely ever seen him not wearing a football top. And I rarely see him wearing the same one twice!”
Clifford, whose fascinating story features bringing Socrates to Garforth Town and working for Sir Clive Woodward’s Southampton and perhaps deserves a book of its own, spent time analysing Gray’s matches at Rotherham and watched him grow. He featured mainly from the left and thrived in moments, though it is down the middle that many see his future.
“He'll be wanting to take the ball, he'll be wanting to make things happen..”
Davis remembers a young man of high individual standards, recalling watching him berate himself for failing to hit the target from an impossible angle while wandering away from a warm-up at Exeter City. Hamshaw sees a youthful integrity behind the confidence and exuberance, citing an example of him going ‘absolutely spare’ at him and teammate Jack Holmes having been found kicking a ball about bare foot in the Roundwood gym.
Where many other players may have sought to avoid all contact with their manager after a public dressing-down, Gray took it upon himself to head up to his office in a quieter moment to apologise and talk it out.
Hamshaw said: “As a young player that it takes a bit of character to do that, the fact that he knew he was in the wrong and faced up to it, it speaks volumes about him as a lad. He’s confident and will back himself, nothing that you wouldn't really expect from a 17-year-old lad really who's obviously done unbelievably well and not probably had that projection or disappointment in football. Ultimately his journey will be up and down as all careers are.
League One.
Rotherham United v Northampton Town.
Millers Matt Hamshaw congratulates Harry Gray on his goal.
27th January 2026..
Picture Jonathan Gawthorpeplaceholder image
League One. Rotherham United v Northampton Town. Millers Matt Hamshaw congratulates Harry Gray on his goal. 27th January 2026.. Picture Jonathan Gawthorpe | National World
“When you're top of the league and you're playing really well and everything's going great around you, football's the easiest game in the world. I've been there at Hillsborough after 25 minutes when it's 0-0 or you're 1-0 down and it gets a bit shaky. Let me tell you, that will not bother Harry Gray. He'll be wanting to take the ball, he'll be wanting to make things happen.
“His experience last year and will make him realise the toughness of League One, the physicality of it. He obviously got stronger while he was at Rotherham but I've expected him to work even harder on his programme over the summer. I think Wednesday will see the benefits of that loan but I just think he's a good character, he's from a good family, he's a great lad.
“I just think he's a player that the Wednesday fans will love because he wants to take people on, he wants to get shots off, but more important than that for me, in South Yorkshire particularly, is that he works really hard for the players around him. You don’t get folk from Barcelona and AC Milan coming to watch someone that doesn’t have big, big potential.”
So it seems representatives from the great and good of European football may well be welcomed to Hillsborough this season. Those close to the short but bustling young career of Harry Gray suggest there’s excitement to be had.
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