Sold at £21.2m, then became a "Rolls-Royce": Levy made big error on Spurs' next Modric - opinion

Tottenham Hotspur are no strangers to transfer heartbreak, with one notable missed opportunity in recent times having been that of current Wolverhampton Wanderers maestro Joao Moutinho.

The veteran Portuguese midfielder continues to delight the Premier League as the heartbeat of Bruno Lage’s side, having showcased his unerring ball-playing talent on a weekly basis since his shock £5m arrival at Molineux in 2018.

The 35-year-old playmaker could have arrived in English football much earlier, though, with Spurs pursuing a deal for the then-Porto man a decade ago as Daniel Levy and co sought a replacement for Real Madrid-bound Luka Modric.

In his first summer in charge, former Chelsea manager Andre Villas-Boas identified his compatriot as the perfect replacement for the departing Croatian, having previously coached the diminutive midfielder during his time in Portugal.

Moutinho had been vital to the youthful coach winning the treble in a remarkable unbeaten campaign during the 2010/11 season – his only one in charge at the Estadio do Dragao – with Villas-Boas desperate for a reunion in north London.

A deal appeared set to be done as Spurs agreed a then club-record fee of £22m for the former Sporting Lisbon man in the summer of 2012, only for the deal to collapse late on transfer deadline day as negotiations broke down with the player’s representatives.

As the 5 foot 7 gem has since admitted, he had just been a matter of “minutes” away from making the move to White Hart Lane, only for the club to see their hopes dashed in brutal fashion right at the climax of the transfer window.

That failure to get the deal done has no doubt come back to bite the Lilywhites, with the Barreiro native eventually joining Monaco in a £21.5m deal