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Transfers
| Player (age) | From club | To club | Date | Fee | |||
|---|---|---|---|---|---|---|---|
| Fees in euro (EUR) | |||||||
| 1 |  C. Ziege (27) |  Milan |  Middlesbrough | 1999, Jul | 6 000 000 | ||
| 2 |  P. Ince (31) |  Liverpool | Middlesbrough | 1999, Jul | 1 500 000 | ||
| 3 | S. Baker (20) | Middlesbrough | 1999, May | ||||
| 4 | B. Roberts (23) |  Millwall | Middlesbrough | 1999, May | |||
| 5 | M. Hudson (18) | FC Middlesbrough U18 | Middlesbrough | 1999, Jul | |||
| 6 |  S. Prunty (19) | FC Middlesbrough U18 | Middlesbrough | 1999, Jul | |||
| 7 |  C. Bennion (18) |  Heart of Midlothian FC U20 | Middlesbrough | 1999, Jul | |||
| 8 | S. Baker (21) |  Huddersfield Town | Middlesbrough | 1999, Sep | |||
| 9 |  J. Paulista (26) |  Atlético | Middlesbrough | 2000, Jan | |||
| 10 | B. Roberts (24) |  Luton Town | Middlesbrough | 2000, Mar | |||
| Player (age) | From club | To club | Date | Fee | |||
|---|---|---|---|---|---|---|---|
| Fees in euro (EUR) | |||||||
| 1 | J. Paulista (26) | Middlesbrough | Atlético | 1999, Jul | 13 800 000 | ||
| 2 |  M. Beck (26) | Middlesbrough |  Derby | 1999, Jul | 700 000 | ||
| 3 | A. Townsend (36) | Middlesbrough |  West Bromwich | 1999, Sep | 50 000 | ||
| 4 | S. Baker (21) | Middlesbrough | 2000, Mar | ||||
| 5 | A. Armstrong (25) | Middlesbrough | Huddersfield Town | 2000, Mar | |||
| 6 | B. Roberts (24) | Middlesbrough | Luton Town | 2000, Feb | |||
| 7 |  V. Kinder (30) | Middlesbrough | 2000, Jan | ||||
| 8 | M. Cummins (21) | Middlesbrough | 2000, Jan | ||||
| 9 | S. Baker (20) | Middlesbrough | Huddersfield Town | 1999, Aug | |||
| 10 | R. Harrower (16) | Middlesbrough | 1999, Jul | ||||
| 11 |  M. Branca (34) | Middlesbrough |  FC Luzern | 1999, Jul | |||
| 12 |  C. Blackmore (34) | Middlesbrough |  Barnsley | 1999, Jul | |||
| 13 |  G. Lombardi (23) | Middlesbrough |  River Plate | 1999, Jul | |||