| 16 Oct 08 | B. Alnwick Ben Alnwick |  Tottenham HotspurTOT | → |  Carlisle UnitedCAR | Loan |
| 25 Sept 08 | A. Barcham Andy Barcham | Tottenham HotspurTOT | → |  GillinghamGIL | Loan |
| 19 Sept 08 | D. Button David Button | Tottenham HotspurTOT | → |  Grays AthleticGrays Ath | Loan |
| 01 Sept 08 | V. Corluka Vedran Corluka |  Manchester CityMNC | → | Tottenham HotspurTOT | 8500000 |
| 01 Sept 08 | R. Pavlyuchenko Roman Pavlyuchenko |  Spartak MoscowSPM | → | Tottenham HotspurTOT | 13800000 |
| 01 Sept 08 | D. Berbatov Dimitar Berbatov | Tottenham HotspurTOT | → |  Manchester UnitedMAN | 30750000 |
| 01 Sept 08 | F. Campbell Fraizer Campbell | Manchester UnitedMAN | → | Tottenham HotspurTOT | Loan |
| 27 Aug 08 | L. Young-Pyo Lee Young-Pyo | Tottenham HotspurTOT | → |  Borussia DortmundDOR | Undisclosed |
| 27 Aug 08 | L. Young-Pyo Lee Young-Pyo | Tottenham HotspurTOT | → | Borussia DortmundDOR | Undisclosed |
| 26 Aug 08 | C. Daniels Charlie Daniels | Tottenham HotspurTOT | → | GillinghamGIL | Loan |
| 26 Aug 08 | T. Pekhart Tomás Pekhart | Tottenham HotspurTOT | → |  SouthamptonSOU | Loan |
| 26 Aug 08 | T. Pekhart Tomás Pekhart | Tottenham HotspurTOT | → | SouthamptonSOU | Loan |
| 14 Aug 08 | A. Gardner Anthony Gardner | Tottenham HotspurTOT | → |  Hull CityHUL | 2500000 |
| 12 Aug 08 | C. Sánchez Dominguez César |  Real ZaragozaZAR | → | Tottenham HotspurTOT | Free |
| 11 Aug 08 | Y. Kaboul Younes Kaboul | Tottenham HotspurTOT | → |  PortsmouthPOR | Undisclosed |
| 08 Aug 08 | T. Archibald-Henville Troy Archibald-Henville | Tottenham HotspurTOT | → |  Norwich CityNOR | Loan |
| 08 Aug 08 | T. Archibald-Henville Troy Archibald-Henville | Tottenham HotspurTOT | → | Norwich CityNOR | Loan |
| 08 Aug 08 | L. Mills Leigh Mills | Tottenham HotspurTOT | → | GillinghamGIL | Loan |
| 30 Jul 08 | D. Bentley David Bentley |  Blackburn RoversBLK | → | Tottenham HotspurTOT | Undisclosed |
| 29 Jul 08 | A. Gardner Anthony Gardner | Tottenham HotspurTOT | → | Hull CityHUL | Loan |
| 28 Jul 08 | R. Keane Robbie Keane | Tottenham HotspurTOT | → |  LiverpoolLIV | 19000000 |
| 26 Jul 08 | P. Chimbonda Pascal Chimbonda | Tottenham HotspurTOT | → |  SunderlandSUN | Undisclosed |
| 25 Jul 08 | P. Robinson Paul Robinson | Tottenham HotspurTOT | → | Blackburn RoversBLK | 3500000 |
| 23 Jul 08 | T. Tainio Teemu Tainio | Tottenham HotspurTOT | → | SunderlandSUN | Undisclosed |
| 07 Jul 08 | T. Forecast Tommy Forecast | Tottenham HotspurTOT | → | SouthamptonSOU | Undisclosed |
| 07 Jul 08 | T. Forecast Tommy Forecast | Tottenham HotspurTOT | → | SouthamptonSOU | Undisclosed |
| 03 Jul 08 | J. Martin Joseph Martin | Tottenham HotspurTOT | → |  BlackpoolBLP | Undisclosed |
| 03 Jul 08 | J. Martin Joseph Martin | Tottenham HotspurTOT | → | BlackpoolBLP | Undisclosed |
| 02 Jul 08 | S. Dawkins Simon Dawkins | Tottenham HotspurTOT | → |  Leyton OrientLEY | Loan |
| 01 Jul 08 | Paul-Jose Mpoku |  Standard LiegeSTL | → | Tottenham HotspurTOT | Undisclosed |
| 01 Jul 08 | L. Modric Luka Modric | DZXDinamo ZagrebDinamo Zagreb | → | Tottenham HotspurTOT | Undisclosed |
| 17 Jun 08 | L. Mills Leigh Mills | Tottenham HotspurTOT | → |  BrentfordBRE | Loan |
| 10 Jun 08 | G. Dos Santos Giovani Dos Santos |  BarcelonaBAR | → | Tottenham HotspurTOT | 4700000 |
| 10 Jun 08 | G. Dos Santos Giovani Dos Santos | BarcelonaBAR | → | Tottenham HotspurTOT | 4700000 |
| 13 May 08 | R. Cerny Radek Cerny | Tottenham HotspurTOT | → |  Queens Park RangersQPR | Free |
| 13 May 08 | R. Cerny Radek Cerny | Tottenham HotspurTOT | → | Queens Park RangersQPR | Free |
| 27 Mar 08 | J. Martin Joseph Martin | Tottenham HotspurTOT | → | BlackpoolBLP | Loan |
| 27 Mar 08 | D. Button David Button | Tottenham HotspurTOT | → |  RochdaleROCH | Loan |
| 27 Mar 08 | J. Martin Joseph Martin | Tottenham HotspurTOT | → | BlackpoolBLP | Loan |
| 31 Jan 08 | G. Melo Gilberto Melo |  Hertha BerlinHERT | → | Tottenham HotspurTOT | Undisclosed |
| 31 Jan 08 | P. Stalteri Paul Stalteri | Tottenham HotspurTOT | → |  FulhamFUL | Loan |
| 31 Jan 08 | A. Gardner Anthony Gardner | Tottenham HotspurTOT | → |  EvertonEVE | Loan |
| 31 Jan 08 | J. Defoe Jermain Defoe | Tottenham HotspurTOT | → | PortsmouthPOR | Loan |
| 31 Jan 08 | G. Melo Gilberto Melo | Hertha BerlinHERT | → | Tottenham HotspurTOT | Undisclosed |
| 30 Jan 08 | A. Hutton Alan Hutton |  RangersRAN | → | Tottenham HotspurTOT | Undisclosed |
| 30 Jan 08 | W. Routledge Wayne Routledge | Tottenham HotspurTOT | → |  Aston VillaAVL | Undisclosed |
| 30 Jan 08 | A. Hutton Alan Hutton | RangersRAN | → | Tottenham HotspurTOT | Undisclosed |
| 28 Jan 08 | J. Woodgate Jonathan Woodgate |  MiddlesbroughMID | → | Tottenham HotspurTOT | Undisclosed |
| 25 Jan 08 | L. Barnard Lee Barnard | Tottenham HotspurTOT | → |  Southend UnitedSOUT | Undisclosed |
| 11 Jan 08 | H. Ghaly Hossam Ghaly | Tottenham HotspurTOT | → |  Derby CountyDER | Loan |
| 11 Jan 08 | H. Ghaly Hossam Ghaly | Tottenham HotspurTOT | → | Derby CountyDER | Loan |
| 10 Jan 08 | P. Ifil Philip Ifil | Tottenham HotspurTOT | → |  Colchester UnitedCOL | Undisclosed |
| 10 Jan 08 | D. Button David Button | Tottenham HotspurTOT | → | Grays AthleticGrays Ath | Loan |
| 07 Jan 08 | B. Alnwick Ben Alnwick | Tottenham HotspurTOT | → |  Leicester CityLEI | Loan |
| 01 Jan 08 | C. Gunter Chris Gunter |  Cardiff CityCAR | → | Tottenham HotspurTOT | Undisclosed |
| 01 Jan 08 | C. Gunter Chris Gunter | Cardiff CityCAR | → | Tottenham HotspurTOT | Undisclosed |