Anfield Insights

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Anfield Insights
Anfield Insights
A look at Ollie O'Connor
Academy

A look at Ollie O'Connor

The 16-year-old Scouser was in fine form on Wednesday afternoon in a rare Liverpool U18 victory.

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Leo Rutherford
Apr 26, 2025
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Anfield Insights
Anfield Insights
A look at Ollie O'Connor
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Scouse midfielders to come through the Liverpool academy, you say? Not many spring to mind. Jay Spearing surely the flagbearer with his fine silver Carling Cup medal from 2012 under Kenny Dalglish? Who can forget then-17-year-old Jordan Rossiter’s finish against Middlesbrough just seven minutes into his debut? Outside of that, I’m stumped.

Ste from Huyton and Ste from Bootle had a little bit of ability, in fairness. Gerrard’s journey from Whiston Juniors to the hallowed Anfield turf, including a trial at Manchester United to force the Reds’ hand over an improved deal, has been well documented. Under the mentorship of legend Steve Heighway, Stevie G overcame the persistent groin and back injuries to pen his first professional deal at the back end of 1997. As they say, the rest was history.

McManaman, well before taking on his current ear-torturing role at TNT Sports, was a blue converted into a red. Macca idolised Evertonians Duncan McKenzie and Bob Latchford but would ultimately be lured over to the bright side of Stanley Park with his dad encouraging Liverpool’s apprentice contract. Two years later, a teenage Steve became professional at Liverpool in February of 1990 - Kenny Dalglish’s final season as manager. An impressive nine-year spell at the club before opting for the ‘new challenge’ in Madrid would follow. Eight major trophies in the nine years after he departed compared to the mere FA Cup and League Cup triumphs in the equivalent period in which Macca was a Red. Not bitter, I swear.

Enough about the past. Curtis Jones and Tyler Morton embody the blueprint from the current Liverpool contingent; the Toxteth and Wallasey-born midfielders have represented their boyhood club on the grandest stages and lifted some of the biggest prizes in the game. The pair also reached the summit in the academy world: Jones, in the wake of Gerrard’s coaching, spearheaded Liverpool’s Youth Cup triumph in 2018/19 before Morton was an integral cog in the LFC side who were narrowly defeated by Villa in the 2021 final.

There’s more bubbling beneath the surface in this (niche) department. Last summer’s scholarship intake features four Scousers - all of whom have been at the club since pre-secondary school. 17-year-old DJ Esdaille, who joined the club at U10 level, is of course a right back but the three other local boys — Joe Upton, Ryan Cowley and Oliver O’Connor — all specialise in central midfield. The pick of the bunch, with the most maiden-year minutes to show for it, is the 16 y/o O’Connor who has been on the club’s books for over ten years.

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