Jack Grealish — Aston Villa to Manchester City (2021) — £100 million

Jack Grealish's £100 million transfer from Aston Villa to Manchester City in August 2021 was the most expensive transfer in Premier League history. City paid the fee despite Grealish starting only 40% of their league games in his first three seasons — a fact that led to widespread debate about squad rotation under Pep Guardiola and whether the fee represented value. He won the Premier League, FA Cup, and Champions League in 2023, making him one of the few £100 million players to directly contribute to a domestic and European treble.