Liverpool sold Philippe Coutinho to Barcelona for a fee of €135 million back in 2018. He's the most expensive sale of all time in premier league history. However, Coutinho is one of the worst signings in Barcelona's history. 
He dropped considerably in performance after joining the Catalan club and was loaned out to Bayern Munich before joining Aston Villa permanently. Barcelona signed Coutinho for a huge fee but the Brazilian forward didn't live up to their expectations.
Manchester City bought Jack Grealish from Aston Villa for a fee of €118 million and he's their most expensive signing of all time. Grealish struggled in his first arrival to City but has managed to establish himself as one of the best wingers in the premier league. The England international has continued to put on impressive performances for his side. 
Chelsea sold Hazard to Real Madrid in 2020 for a fee of €115 million. He was one of the best wingers in the premier league during his time at Chelsea but dropped considerably in performance after joining the Los blancos. Hazard is currently among the worst wingers in the top five European leagues and his future at Real Madrid remains unclear.
Tottenham Hotspur sold Bale to Real Madrid in 2014 for a fee of €101 million and he went on to become one of the best wingers of all time.
Manchester United sold Cristiano Ronaldo to Real Madrid in 2009 for a fee of €94 million. The Red devils spent €85 million on signing Maguire from Leicester City in 2018 and they also spent €85 million on signing Romelu Lukaku from Everton.
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