Leeds United academy product Jamie Shackleton left the club on a free transfer in 2024, joining Sheffield United following over 17 years with the club.
Jamie Shackleton joined his boyhood club in 2006, coming through the Thorp Arch ranks and going on to make 94 Leeds United appearances between 2018 and 2024.
The utility man can operate as a central midfielder, defensive midfielder, right-back, but also as a right-sided wing back or winger. His positional versatility has seen him deployed in each of those roles for Leeds and Sheffield United as well.
It was under Marcelo Bielsa’s tutelage that he first broke through at Elland Road, but Daniel Farke allowed the 26-year-old to depart on a free transfer after the 2023/24 campaign. Shackleton appeared in just 15 games under Farke.
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Jamie Shackleton’s Instagram reaction to Sheffield United return
He has had an injury-ravaged few years now, having made 37 appearances for Millwall in 2022/23. Following that loan spell, it has been 15 and 12 games played in the last two campaigns.
Shackleton joined the Blades from Leeds after rejecting a new deal. However, now, in 2025/26, Shackleton made his return to action. He came on in the 82nd minute of Saturday’s game against Javia Gracia’s Watford.
It was a difficult first campaign at Bramall Lane for Shackleton, starting just two of the 12 league games he appeared in. But much like Shackleton’s Leeds exit, it was emotional on Saturday for the 26-year-old.
His side won 1-0 for their second league victory of the campaign, but it also marked a 308-day wait since his last professional appearance. He played in a 2-0 win against Plymouth Argyle mid-December for his last game for the club.
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Shackleton reacted to his return on his Instagram story, stating: “Physically and mentally the toughest spell I’ve faced. What a feeling being back on the football pitch!! 3 points to go with it ⚔️”
It’s been a difficult time in South Yorkshire for him and for the club of late, who still sit 23rd after their second win in 10 league outings.
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Chris Wilder’s praise of Marcelo Bielsa for Jamie Shackleton’s development
Speaking in his pre-match press conference via The Star, Chris Wilder said: “He’s been pretty unfortunate with his injuries last season and he picked up an injury pre-season as well so it’s good to see him back.
“He’s an infectious, enthusiastic player. Just look at his appearances in the Premier League for Leeds under Bielsa, so for Marcelo to trust him in the Premier League, he’s a good player. He’s been frustrated, we’ve been frustrated but he’s come through Tuesday afternoon.
“He’s got 45 minutes so he’ll be involved or be in the squad on Saturday so that’s a bonus for him and us.”
Bielsa, speaking in 2020 via Leeds Live, said: “In the case of Shackleton he’s played in the first team before and every time he has played, he has played with personality and done a good job.”