| 16 Oct 14 | M. Veljkovic Milos Veljkovic |  Tottenham HotspurTOT | → |  MiddlesbroughMID | Loan |
| 16 Oct 14 | M. Veljkovic Milos Veljkovic | Tottenham HotspurTOT | → | MiddlesbroughMID | Loan |
| 01 Sept 14 | E. Fryers Ezekiel Fryers | Tottenham HotspurTOT | → |  Crystal PalaceCRY | Undisclosed |
| 01 Sept 14 | B. Stambouli Benjamin Stambouli |  MontpellierMONT | → | Tottenham HotspurTOT | Undisclosed |
| 01 Sept 14 | L. Holtby Lewis Holtby | Tottenham HotspurTOT | → |  Hamburg SVHSV | Loan |
| 01 Sept 14 | J. Obika Jonathan Obika | Tottenham HotspurTOT | → |  Swindon TownSWI | Undisclosed |
| 01 Sept 14 | Sandro | Tottenham HotspurTOT | → |  Queens Park RangersQPR | Undisclosed |
| 01 Sept 14 | S. Coulibaly Souleymane Coulibaly | Tottenham HotspurTOT | → |  BariBAR | Loan |
| 01 Sept 14 | L. Holtby Lewis Holtby | Tottenham HotspurTOT | → | Hamburg SVHSV | Loan |
| 01 Sept 14 | B. Stambouli Benjamin Stambouli | MontpellierMONT | → | Tottenham HotspurTOT | Undisclosed |
| 28 Aug 14 | R. Fredericks Ryan Fredericks | Tottenham HotspurTOT | → | MiddlesbroughMID | Loan |
| 28 Aug 14 | R. Fredericks Ryan Fredericks | Tottenham HotspurTOT | → | MiddlesbroughMID | Loan |
| 27 Aug 14 | F. Fazio Federico Fazio |  SevillaSEV | → | Tottenham HotspurTOT | Undisclosed |
| 27 Aug 14 | F. Fazio Federico Fazio | SevillaSEV | → | Tottenham HotspurTOT | Undisclosed |
| 26 Aug 14 | M. Dawson Michael Dawson | Tottenham HotspurTOT | → |  Hull CityHUL | Undisclosed |
| 22 Aug 14 | T. Carroll Thomas Carroll | Tottenham HotspurTOT | → |  Swansea CitySWA | Loan |
| 13 Aug 14 | D. Yedlin DeAndre Yedlin |  Seattle Sounders FCSEA | → | Tottenham HotspurTOT | Undisclosed |
| 13 Aug 14 | D. Yedlin DeAndre Yedlin | Tottenham HotspurTOT | → | Seattle Sounders FCSEA | Loan |
| 13 Aug 14 | D. Yedlin DeAndre Yedlin | Seattle Sounders FCSEA | → | Tottenham HotspurTOT | Undisclosed |
| 13 Aug 14 | D. Yedlin DeAndre Yedlin | Tottenham HotspurTOT | → | Seattle Sounders FCSEA | Loan |
| 05 Aug 14 | J. Archer Jordan Archer | Tottenham HotspurTOT | → |  Northampton TownNHT | Loan |
| 04 Aug 14 | S. Coulthirst Shaquile Coulthirst | Tottenham HotspurTOT | → |  Southend UnitedSOUT | Loan |
| 02 Aug 14 | E. Dier Eric Dier |  Sporting CPSCP | → | Tottenham HotspurTOT | Undisclosed |
| 01 Aug 14 | I. Falque Iago Falque | Tottenham HotspurTOT | → |  GenoaGEN | Undisclosed |
| 01 Aug 14 | I. Falque Iago Falque | Tottenham HotspurTOT | → | GenoaGEN | Undisclosed |
| 24 Jul 14 | K. McEvoy Kenneth McEvoy | Tottenham HotspurTOT | → |  Peterborough UnitedPET | Loan |
| 23 Jul 14 | G. Sigurdsson Gylfi Sigurdsson | Tottenham HotspurTOT | → | Swansea CitySWA | Swap |
| 23 Jul 14 | B. Davies Ben Davies | Swansea CitySWA | → | Tottenham HotspurTOT | Swap |
| 23 Jul 14 | M. Vorm Michel Vorm | Swansea CitySWA | → | Tottenham HotspurTOT | Swap |
| 17 Jul 14 | A. Pritchard Alex Pritchard | Tottenham HotspurTOT | → |  BrentfordBRE | Loan |
| 17 Jul 14 | A. Pritchard Alex Pritchard | Tottenham HotspurTOT | → | BrentfordBRE | Loan |
| 01 Jul 14 | G. Hall Grant Hall | Tottenham HotspurTOT | → |  Birmingham CityBIR | Loan |
| 01 Jul 14 | G. Hall Grant Hall | Tottenham HotspurTOT | → | Birmingham CityBIR | Loan |
| 01 Jul 14 | H. Gomes Heurelho Gomes | Tottenham HotspurTOT | → |  WatfordWAT | Free |
| 01 Jul 14 | H. Gomes Heurelho Gomes | Tottenham HotspurTOT | → | WatfordWAT | Free |
| 25 Jun 14 | J. Livermore Jake Livermore | Tottenham HotspurTOT | → | Hull CityHUL | Undisclosed |
| 27 Mar 14 | S. Coulthirst Shaquile Coulthirst | Tottenham HotspurTOT | → |  Torquay UnitedTQU | Loan |
| 22 Mar 14 | G. Ward Grant Ward | Tottenham HotspurTOT | → |  Chicago Fire FCCHI | Loan |
| 22 Mar 14 | G. Ward Grant Ward | Tottenham HotspurTOT | → | Chicago Fire FCCHI | Loan |
| 17 Mar 14 | J. Obika Jonathan Obika | Tottenham HotspurTOT | → |  Charlton AthleticCHA | Loan |
| 17 Mar 14 | J. Obika Jonathan Obika | Tottenham HotspurTOT | → | Charlton AthleticCHA | Loan |
| 08 Mar 14 | J. Miles Jonathan Miles | Tottenham HotspurTOT | → | WXXWhitehawkWhitehawk | Loan |
| 28 Feb 14 | J. Defoe Jermain Defoe | Tottenham HotspurTOT | → |  Toronto FCTOR | Undisclosed |
| 28 Feb 14 | J. Defoe Jermain Defoe | Tottenham HotspurTOT | → | Toronto FCTOR | Undisclosed |
| 31 Jan 14 | L. Holtby Lewis Holtby | Tottenham HotspurTOT | → |  FulhamFUL | Loan |
| 28 Jan 14 | A. Smith Adam Smith | Tottenham HotspurTOT | → |  AFC BournemouthBOU | Undisclosed |
| 28 Jan 14 | A. Smith Adam Smith | Tottenham HotspurTOT | → | AFC BournemouthBOU | Undisclosed |
| 17 Jan 14 | R. Fredericks Ryan Fredericks | Tottenham HotspurTOT | → |  MillwallMIL | Loan |
| 17 Jan 14 | R. Fredericks Ryan Fredericks | Tottenham HotspurTOT | → | MillwallMIL | Loan |
| 08 Jan 14 | J. Obika Jonathan Obika | Tottenham HotspurTOT | → |  Brighton & Hove AlbionBHA | Loan |
| 08 Jan 14 | J. Obika Jonathan Obika | Tottenham HotspurTOT | → | Brighton & Hove AlbionBHA | Loan |
| 03 Jan 14 | S. Dawkins Simon Dawkins | Tottenham HotspurTOT | → |  Derby CountyDER | Undisclosed |
| 03 Jan 14 | S. Coulthirst Shaquile Coulthirst | Tottenham HotspurTOT | → |  Leyton OrientLEY | Loan |
| 03 Jan 14 | S. Dawkins Simon Dawkins | Tottenham HotspurTOT | → | Derby CountyDER | Undisclosed |