| 27 Nov 08 | C. Birchall Chris Birchall |  Coventry CityCOV | → |  Carlisle UnitedCAR | Loan |
| 27 Nov 08 | G. Borrowdale Gary Borrowdale | Coventry CityCOV | → |  Queens Park RangersQPR | Loan |
| 25 Oct 08 | D. Konstantopoulos Dimitrios Konstantopoulos | Coventry CityCOV | → |  Swansea CitySWA | Loan |
| 17 Oct 08 | W. Andrews Wayne Andrews | Coventry CityCOV | → |  Luton TownLUT | Loan |
| 01 Oct 08 | K. Kyle Kevin Kyle | Coventry CityCOV | → |  Hartlepool UnitedHAR | Loan |
| 26 Sept 08 | G. Borrowdale Gary Borrowdale | Coventry CityCOV | → |  Colchester UnitedCOL | Loan |
| 26 Sept 08 | K. Thornton Kevin Thornton | Coventry CityCOV | → |  Brighton & Hove AlbionBHA | Loan |
| 01 Sept 08 | J. Gray Julian Gray | Coventry CityCOV | → |  FulhamFUL | Loan |
| 01 Sept 08 | J. Gray Julian Gray | Coventry CityCOV | → | FulhamFUL | Loan |
| 13 Aug 08 | D. Simmonds Donovan Simmonds | Coventry CityCOV | → |  KilmarnockKIL | Loan |
| 13 Aug 08 | D. Simmonds Donovan Simmonds | Coventry CityCOV | → | KilmarnockKIL | Loan |
| 08 Aug 08 | S. Wright Stephen Wright | XXX | → | Coventry CityCOV | Free |
| 07 Aug 08 | C. Morrison Clinton Morrison | XXX | → | Coventry CityCOV | Free |
| 11 Jul 08 | F. Eastwood Freddy Eastwood |  Wolverhampton WanderersWOL | → | Coventry CityCOV | 1200000 |
| 18 Jun 08 | K. Westwood Kieren Westwood | Carlisle UnitedCAR | → | Coventry CityCOV | 500000 |
| 17 Jun 08 | A. Gunnarsson Aron Gunnarsson |  AZ AlkmaarAZ | → | Coventry CityCOV | Undisclosed |
| 17 Jun 08 | A. Gunnarsson Aron Gunnarsson | AZ AlkmaarAZ | → | Coventry CityCOV | Undisclosed |
| 06 Jun 08 | L. Davis Liam Davis | Coventry CityCOV | → |  Northampton TownNHT | Free |
| 02 Jun 08 | G. Beuzelin Guillaume Beuzelin |  HibernianHIBS | → | Coventry CityCOV | Free |
| 02 Jun 08 | G. Beuzelin Guillaume Beuzelin | HibernianHIBS | → | Coventry CityCOV | Free |
| 30 May 08 | C. Hawkins Colin Hawkins | Coventry CityCOV | → | Brighton & Hove AlbionBHA | Free |
| 23 May 08 | M. Hudson Mark Hudson | Coventry CityCOV | → |  Charlton AthleticCHA | Free |
| 27 Mar 08 | Z. Hines Zavon Hines |  West Ham UnitedWHU | → | Coventry CityCOV | Loan |
| 27 Mar 08 | C. Hawkins Colin Hawkins | Coventry CityCOV | → |  ChesterfieldCHES | Loan |
| 27 Mar 08 | Z. Hines Zavon Hines | West Ham UnitedWHU | → | Coventry CityCOV | Loan |
| 27 Mar 08 | W. Andrews Wayne Andrews | Coventry CityCOV | → |  Bristol RoversBRI | Loan |
| 27 Mar 08 | Donovan Simmons | Coventry CityCOV | → |  GillinghamGIL | Loan |
| 25 Mar 08 | D. Konstantopoulos Dimitrios Konstantopoulos | Coventry CityCOV | → |  Nottingham ForestFOR | Loan |
| 21 Mar 08 | R. Duffy Richard Duffy |  PortsmouthPOR | → | Coventry CityCOV | Loan |
| 21 Mar 08 | R. Duffy Richard Duffy | PortsmouthPOR | → | Coventry CityCOV | Loan |
| 14 Mar 08 | K. Schmeichel Kasper Schmeichel |  Manchester CityMNC | → | Coventry CityCOV | Loan |
| 14 Mar 08 | K. Schmeichel Kasper Schmeichel | Manchester CityMNC | → | Coventry CityCOV | Loan |
| 31 Jan 08 | D. Adebola Dele Adebola | Coventry CityCOV | → |  Bristol CityBRC | Undisclosed |
| 31 Jan 08 | S. Dann Scott Dann |  WalsallWAL | → | Coventry CityCOV | Undisclosed |
| 30 Jan 08 | K. Kyle Kevin Kyle | Coventry CityCOV | → | Wolverhampton WanderersWOL | Loan |
| 28 Jan 08 | D. Fox Daniel Fox | WalsallWAL | → | Coventry CityCOV | Undisclosed |
| 21 Jan 08 | R. Page Robert Page | Coventry CityCOV | → |  Huddersfield TownHUD | Free |