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 set a Premier League record, yet he started only 40% of league games in his first three seasons, sparking debate about value under Pep Guardiola. Despite this, Grealish contributed directly to City's 2023 treble—Premier League, FA Cup, and Champions League—scoring 14 goals and 18 assists across all competitions. His £100 million fee is 37.5% cheaper than #3 Coutinho's €160 million, yet Grealish's treble achievement makes him one of the few £100 million players to deliver major silverware, outperforming Coutinho's trophy haul at Barcelona.