| 27 Nov 14 | B. Fewster Bradley Fewster |  MiddlesbroughMID | → |  Preston North EndPNE | Loan |
| 22 Nov 14 | E. Ledesma Emmanuel Ledesma | MiddlesbroughMID | → |  Rotherham UnitedROT | Loan |
| 21 Nov 14 | B. Morris Bryn Morris | MiddlesbroughMID | → |  Burton AlbionBRT | Loan |
| 14 Nov 14 | B. Halliday Brad Halliday | MiddlesbroughMID | → |  York CityYORK | Loan |
| 23 Oct 14 | L. Williams Luke Williams | MiddlesbroughMID | → |  Scunthorpe UnitedSCU | Loan |
| 17 Oct 14 | A. Halliday Andy Halliday | MiddlesbroughMID | → |  Bradford CityBRD | Loan |
| 16 Oct 14 | M. Veljkovic Milos Veljkovic |  Tottenham HotspurTOT | → | MiddlesbroughMID | Loan |
| 16 Oct 14 | M. Veljkovic Milos Veljkovic | Tottenham HotspurTOT | → | MiddlesbroughMID | Loan |
| 26 Sept 14 | D. Atkinson David Atkinson | MiddlesbroughMID | → |  Hartlepool UnitedHAR | Loan |
| 01 Sept 14 | S. Hines Seb Hines | MiddlesbroughMID | → |  Coventry CityCOV | Loan |
| 01 Sept 14 | Y. Wildschut Yanic Wildschut |  HeerenveenHEE | → | MiddlesbroughMID | Undisclosed |
| 01 Sept 14 | J. Vossen Jelle Vossen |  Racing GenkGENK | → | MiddlesbroughMID | Undisclosed |
| 01 Sept 14 | Y. Wildschut Yanic Wildschut | HeerenveenHEE | → | MiddlesbroughMID | Undisclosed |
| 01 Sept 14 | J. Blackman Jamal Blackman |  ChelseaCHE | → | MiddlesbroughMID | Loan |
| 01 Sept 14 | J. Vossen Jelle Vossen | Racing GenkGENK | → | MiddlesbroughMID | Loan |
| 01 Sept 14 | J. Steele Jason Steele | MiddlesbroughMID | → |  Blackburn RoversBLK | Loan |
| 01 Sept 14 | J. Blackman Jamal Blackman | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 30 Aug 14 | P. Bamford Patrick Bamford | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 30 Aug 14 | P. Bamford Patrick Bamford | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 28 Aug 14 | R. Fredericks Ryan Fredericks | Tottenham HotspurTOT | → | MiddlesbroughMID | Loan |
| 28 Aug 14 | R. Fredericks Ryan Fredericks | Tottenham HotspurTOT | → | MiddlesbroughMID | Loan |
| 22 Aug 14 | R. Smallwood Richard Smallwood | MiddlesbroughMID | → | Rotherham UnitedROT | Undisclosed |
| 21 Aug 14 | C. Burgess Christian Burgess | MiddlesbroughMID | → |  Peterborough UnitedPET | Undisclosed |
| 21 Aug 14 | Charlie Wyke | MiddlesbroughMID | → | Hartlepool UnitedHAR | Loan |
| 19 Aug 14 | R. Smallwood Richard Smallwood | MiddlesbroughMID | → | Rotherham UnitedROT | Loan |
| 19 Aug 14 | C. Burgess Christian Burgess | MiddlesbroughMID | → | Peterborough UnitedPET | Loan |
| 16 Aug 14 | D. Abella Pérez Damia |  OsasunaOSA | → | MiddlesbroughMID | Undisclosed |
| 13 Aug 14 | A. Clayton Adam Clayton |  Huddersfield TownHUD | → | MiddlesbroughMID | Swap |
| 13 Aug 14 | J. Butterfield Jacob Butterfield | MiddlesbroughMID | → | Huddersfield TownHUD | Swap |
| 08 Aug 14 | R. Brobbel Ryan Brobbel | MiddlesbroughMID | → | Hartlepool UnitedHAR | Loan |
| 06 Aug 14 | K. Omeruo Kenneth Omeruo | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 06 Aug 14 | K. Omeruo Kenneth Omeruo | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 01 Aug 14 | E. Nsue Emilio Nsue |  MallorcaMLL | → | MiddlesbroughMID | Undisclosed |
| 30 Jul 14 | J. Husband James Husband |  Doncaster RoversDON | → | MiddlesbroughMID | Undisclosed |
| 30 Jul 14 | C. Main Curtis Main | MiddlesbroughMID | → | Doncaster RoversDON | Undisclosed |
| 15 Jul 14 | L. Jutkiewicz Lukas Jutkiewicz | MiddlesbroughMID | → |  BurnleyBUR | Undisclosed |
| 15 Jul 14 | L. Jutkiewicz Lukas Jutkiewicz | MiddlesbroughMID | → | BurnleyBUR | Undisclosed |
| 14 Jul 14 | E. García Enrique García | MXXMurciaMUR | → | MiddlesbroughMID | Undisclosed |
| 04 Jul 14 | T. Mejias Tomas Mejias |  Real MadridMAD | → | MiddlesbroughMID | Undisclosed |
| 04 Jul 14 | T. Mejias Tomas Mejias | Real MadridMAD | → | MiddlesbroughMID | Undisclosed |
| 02 Jul 14 | M. Emnes Marvin Emnes | MiddlesbroughMID | → |  Swansea CitySWA | Undisclosed |
| 02 Jul 14 | M. Emnes Marvin Emnes | MiddlesbroughMID | → | Swansea CitySWA | Undisclosed |
| 01 Jul 14 | F. Richardson Frazer Richardson | MiddlesbroughMID | → | Rotherham UnitedROT | Free |
| 27 Mar 14 | R. Brobbel Ryan Brobbel | MiddlesbroughMID | → | York CityYORK | Loan |
| 03 Mar 14 | C. Ripley Connor Ripley | MiddlesbroughMID | → | SFXÖstersunds FKÖstersunds FK | Loan |
| 28 Feb 14 | W. Kneeshaw Wilson Kneeshaw | MiddlesbroughMID | → | APTACS Poli TimisoaraACS Poli Timisoara | Undisclosed |
| 27 Feb 14 | C. Park Cameron Park | MiddlesbroughMID | → |  Crewe AlexandraCREW | Loan |
| 18 Feb 14 | L. Tomlin Lee Tomlin | Peterborough UnitedPET | → | MiddlesbroughMID | Undisclosed |
| 08 Feb 14 | M. Dolan Matthew Dolan | MiddlesbroughMID | → | Bradford CityBRD | Loan |
| 31 Jan 14 | T. Mejías Tomás Mejías | Real MadridMAD | → | MiddlesbroughMID | Loan |
| 31 Jan 14 | D. Graham Danny Graham |  SunderlandSUN | → | MiddlesbroughMID | Loan |
| 31 Jan 14 | L. Tomlin Lee Tomlin | Peterborough UnitedPET | → | MiddlesbroughMID | Loan |
| 31 Jan 14 | T. Mejías Tomás Mejías | Real MadridMAD | → | MiddlesbroughMID | Loan |
| 31 Jan 14 | D. Graham Danny Graham | SunderlandSUN | → | MiddlesbroughMID | Loan |
| 31 Jan 14 | M. Emnes Marvin Emnes | MiddlesbroughMID | → | Swansea CitySWA | Loan |
| 31 Jan 14 | F. Haroun Faris Haroun | MiddlesbroughMID | → |  BlackpoolBLP | Free |
| 31 Jan 14 | M. Emnes Marvin Emnes | MiddlesbroughMID | → | Swansea CitySWA | Loan |
| 28 Jan 14 | L. Jutkiewicz Lukas Jutkiewicz | MiddlesbroughMID | → |  Bolton WanderersBOL | Loan |
| 27 Jan 14 | F. Richardson Frazer Richardson | MiddlesbroughMID | → |  Ipswich TownIPS | Loan |
| 24 Jan 14 | A. Halliday Andy Halliday | MiddlesbroughMID | → | BlackpoolBLP | Loan |
| 24 Jan 14 | D. Ayala Daniel Ayala |  Norwich CityNOR | → | MiddlesbroughMID | Undisclosed |
| 24 Jan 14 | D. Ayala Daniel Ayala | Norwich CityNOR | → | MiddlesbroughMID | Undisclosed |
| 23 Jan 14 | R. Smallwood Richard Smallwood | MiddlesbroughMID | → | Rotherham UnitedROT | Loan |
| 23 Jan 14 | L. Williams Luke Williams | MiddlesbroughMID | → | Hartlepool UnitedHAR | Loan |
| 23 Jan 14 | A. Reach Adam Reach | MiddlesbroughMID | → | Bradford CityBRD | Loan |
| 16 Jan 14 | N. Chalobah Nathaniel Chalobah | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 16 Jan 14 | N. Chalobah Nathaniel Chalobah | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 07 Jan 14 | K. Omeruo Kenneth Omeruo | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 07 Jan 14 | K. Omeruo Kenneth Omeruo | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 03 Jan 14 | C. Wyke Charlie Wyke | MiddlesbroughMID | → |  AFC WimbledonWIM | Loan |
| 02 Jan 14 | J. Hoyte Justin Hoyte | MiddlesbroughMID | → |  MillwallMIL | Undisclosed |