Manchester United had two golden transfer opportunities - but Real Madrid beat them to both

Manchester United's midfield overhaul is into its latest inception with the summer arrival of Manuel Ugarte and the breakthrough of Kobbie Mainoo.

United have been searching for balance and talent ever since Sir Alex Ferguson left and now it's the turn of the 2024 interpretation to stake a claim at being the long-term solution.

It's long been a problem position for United - but then replacing players like Michael Carrick and Paul Scholes was never going to be an easy task. But as United have fallen from being one of Europe's best and most feared sides, their recent transfer history is littered with what-might-have-beens.

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And tonight, in arguably Europe's biggest club football contest, when heavyweights Real Madrid and Barcelona meet, United will be reminded of two players who could, had things worked out differently, been preparing for West Ham away instead of El Clasico.

Thirteen years ago Luka Modric was targeted by United in the aftermath of the 2011 Champions League final at Wembley when Sir Alex Ferguson's side had been well and truly beaten by Barcelona.

The Reds wanted to replicate what Barca had managed to achieve in that eye-opening contest and Modric was identified. But the well-known frosty relationship between United and Spurs chairman Daniel Levy meant a deal was difficult.

Modric stayed put but United remained keen. Yet when he did move a year later it was to Spain, not Manchester.

Real Madrid struck a deal with the Croatian midfielder, despite a willingness on Modric's part to move to Old Trafford. In the end United signed Shinji Kagawa and the rest is history.

Indeed Modric made his mark in the Spanish capital this week when he became Madrid's oldest player and he is still a key part of the squad now, at 39. He did so alongside Jude Bellingham, another top midfielder who United coveted, courted and missed out on.

United were in the race for the talented teenager as some of the world's biggest clubs battled for the Birmingham City star's signature.

Ferguson was drafted in by then United boss Ole Gunnar Solksjaer to help sell the club. Bellingham was given the red carpet treatment as a 17-year-old but he ended up choosing Dortmund. Madrid subsequently signed him from the Bundesliga club, with United by that stage not a serious option for one of the world's best players.

Now 21, Bellingham and Modric are at opposite ends of their careers but they could dovetail against Barcelona in El Clasico tonight. It's a case of what might have been for United.