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| Player (age) | From club | To club | Date | Fee | |||
|---|---|---|---|---|---|---|---|
| Show/hide all additional info | Fees in euro (EUR) | ||||||
| 1 |  |  A. Traoré (22) |  Middlesbrough |  Wolverhampton | 2018, Aug | 20 000 000 | |
| 2 |  |  B. Gibson (25) | Middlesbrough |  Burnley | 2018, Aug | 16 900 000 | |
| 3 |  |  Y. Aiyegbeni (24) | Middlesbrough |  Everton | 2007, Aug | 16 500 000 | |
| 4 |  | D. Spence (21) | Middlesbrough |  Tottenham | 2022, Jul | 14 700 000 | |
| 5 | |  J. Paulista (26) | Middlesbrough |  Atlético | 1999, Jul | 13 800 000 | |
| 6 |  |  M. de Roon (26) | Middlesbrough |  Atalanta | 2017, Aug | 13 500 000 | |
| 7 |  | S. Downing (25) | Middlesbrough |  Aston Villa | 2009, Jul | 13 000 000 | |
| 8 |  | A. Alves (28) | Middlesbrough | 2009, Sep | 12 000 000 | ||
| 9 | | M. Tavernier (23) | Middlesbrough |  Bournemouth | 2022, Aug | 11 900 000 | |
| 10 |  | J. Woodgate (28) | Middlesbrough | Tottenham | 2008, Jan | 10 800 000 | |