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Transfers
| Player (age) | From club | To club | Date | Fee | |||
|---|---|---|---|---|---|---|---|
| Show/hide all additional info | Fees in euro (EUR) | ||||||
| 1 |  B. Deane (30) |  Benfica |  Middlesbrough | 1998, Jul | 4 180 000 | ||
| 2 | C. Cooper (31) |  Nottingham | Middlesbrough | 1998, Jul | 3 750 000 | ||
| 3 | G. Pallister (33) |  Man United | Middlesbrough | 1998, Jul | 2 800 000 | ||
| 4 | D. Gordon (25) |  Crystal Palace | Middlesbrough | 1998, Jul | 1 350 000 | ||
| 5 |  J. Gavin (18) | Middlesbrough | 1998, Jun | ||||
| 6 |  L. Wilkshire (16) | Middlesbrough | 1998, Jul | ||||
| 7 |  M. Branca (33) |  Inter | Middlesbrough | 1998, Jul | |||
| 8 |  G. Lombardi (22) | Middlesbrough | 1998, Jul | ||||
| 9 | C. Harrison (21) |  Preston North End | Middlesbrough | 1999, Feb | |||
| Player (age) | From club | To club | Date | Fee | |||
|---|---|---|---|---|---|---|---|
| Show/hide all additional info | Fees in euro (EUR) | ||||||
| 1 |  Émerson (26) | Middlesbrough |  Tenerife | 1998, Jul | 6 400 000 | ||
| 2 | P. Merson (30) | Middlesbrough |  Aston Villa | 1999, Jan | 6 000 000 | ||
| 3 | R. O´Brien (20) | Middlesbrough |  Juventus | 1999, Mar | 900 000 | ||
| 4 | B. Roberts (23) | Middlesbrough |  Millwall | 1999, Feb | |||
| 5 | C. Harrison (21) | Middlesbrough | Preston North End | 1999, Jan | |||
| 6 | C. Hignett (28) | Middlesbrough |  Aberdeen FC | 1998, Jul | |||
| 7 | P. Connor (19) | Middlesbrough |  Stoke | 1998, Jul | |||
| 8 | B. Robson (41) | Middlesbrough | no club | 1998, Jul | |||
| 9 | N. Pearson (34) | Middlesbrough | no club | 1998, Jul | |||