| League One (Tier Three) Honours | ||||||||||
| Season | Win/R U | Name | Surname | Chr Name | Club | App | Sub | Goals | Notes | |
| 1959/60 | Runner Up | Roy McCrohan | McCrohan | Roy | Norwich City | - | - | - | ||
| 1962/63 | Winner | John Kurila | Kurila | John | Northampton Town | 40 | 0 | 1 | ||
| 1963/64 | Runner Up | Bert Howe | Howe | Bert | Crystal Palace | - | - | - | ||
| 1963/64 | Runner Up | Brian Wood | Wood | Brian | Crystal Palace | - | - | - | ||
| 1965/66 | Runner Up | Micky Brown | Brown | Micky | Millwall | 28 | 2 | 10 | ||
| 1965/66 | Runner Up | John Gilchrist | Gilchrist | John | Millwall | 46 | 0 | 1 | ||
| 1965/66 | Runner Up | Ken Jones | Jones | Ken | Millwall | 43 | 0 | 3 | ||
| 1968/69 | Winner | Brian Garvey | Garvey | Brian | Watford | 33 | 0 | 0 | ||
| 1968/69 | Winner | Brian Owen | Owen | Brian | Watford | 30 | 1 | 4 | ||
| 1968/69 | Winner | Mike Walker | Walker | Mike | Watford | 42 | 0 | 0 | ||
| 1968/69 | Winner | Johnny Williams | Williams | Johnny | Watford | 44 | 0 | 0 | ||
| 1970/71 | Runner Up | Stan Brown | Brown | Stan | Fulham | - | - | - | ||
| 1975/76 | Winner | Jimmy Lindsay | Lindsay | Jimmy | Hereford United | 46 | 0 | 2 | ||
| 1976/77 | Winner | Ian McDonald | McDonald | Ian | Mansfield Town | - | - | - | ||
| 1977/78 | Winner | John Lyons | Lyons | John | Wrexham | - | - | - | ||
| 1977/78 | Runner Up | Lindsey Smith | Smith | Lindsey | Cambridge United | - | - | - | ||
| 1978/79 | Winner | Jimmy Lindsay | Lindsay | Jimmy | Shrewsbury Town | - | - | - | ||
| 1978/79 | Runner Up | Roger Joslyn | Joslyn | Roger | Watford | 44 | 1 | 8 | ||
| 1979/80 | Runner Up | Glenn Keeley | Keeley | Glenn | Blackburn Rovers | - | - | - | ||
| 1982/83 | Winner | John McLaughlin | McLaughlin | John | Portsmouth | - | - | - | ||
| 1983/84 | Winner | Paul Hinshelwood | Hinshelwood | Paul | Oxford United | 43 | - | - | ||
| 1984/85 | Runner Up | Kevin Bremner | Bremner | Kevin | Millwall | 29 | 8 | 11 | ||
| 1984/85 | Runner Up | Nicky Chatterton | Chatterton | Nicky | MIllwall | 33 | 0 | 3 | ||
| 1984/85 | Runner Up | Paul Hinshelwood | Hinshelwood | Paul | Millwall | 21 | 0 | 0 | ||
| 1984/85 | Runner Up | Lindsay Smith | Smith | Lindsay | MIllwall | 40 | 1 | 5 | ||
| 1985/86 | Winner | Kevin Bremner | Bremner | Kevin | Reading | - | - | - | ||
| 1987/88 | Runner Up | Kevin Bremner | Bremner | Kevin | Brighton & Hove Albion | - | - | - | ||
| 1987/88 | Runner Up | Keith Dublin | Dublin | Keith | Brighton & Hove Albion | 46 | - | - | ||
| 1987/88 | Runner Up | John Keeley | Keeley | John | Brighton & Hove Albion | 46 | 0 | 0 | ||
| 1990/91 | Winner | Michael Cheetham | Cheetham | Michael | Cambridge United | - | - | - | ||
| 1990/91 | Winner | Tony Dennis | Dennis | Tony | Cambridge United | - | - | - | ||
| 1990/91 | Winner | John Taylor | Taylor | John | Cambridge United | - | - | - | ||
| 1990/91 | Winner | John Vaughan | Vaughan | John | Cambridge United | - | - | - | ||
| 1990/91 | Runner Up | Peter Cawley | Cawley | Peter | Southend United | 6 | 1 | 0 | ||
| 1990/91 | Runner Up | Christian Hyslop | Hyslop | Christian | Southend United | 9 | 1 | 0 | ||
| 1990/91 | Runner Up | Adam Locke | Locke | Adam | Southend United | 18 | 2 | 3 | ||
| 1990/91 | Runner Up | Dave Martin | Martin | Dave | Southend United | 35 | 0 | 11 | ||
| 1991/92 | Winner | Graham Benstead | Benstead | Graham | Brentford | - | - | - | ||
| 1992/93 | Runner Up | Tony Kelly | Kelly | Tony | Bolton Wanderers | - | - | - | ||
| 1994/95 | Winner | Dave Barnett | Barnett | Dave | Birmingham City | - | - | - | ||
| 1997/98 | Winner | Alec Chamberlain | Chamberlain | Alec | Watford | 46 | 0 | 0 | ||
| 1997/98 | Winner | Richard Johnson | Johnson | Richard | Watford | 42 | 0 | 7 | ||
| 1997/98 | Runner Up | Adam Locke | Locke | Adam | Bristol City | 36 | 2 | 1 | ||
| 1998/99 | Runner Up | Jimmy Walker | Walker | Jimmy | Walsall | 46 | 0 | 0 | ||
| 2000/01 | Runner Up | Guy Branston | Branston | Guy | Rotherham United | 41 | 0 | 6 | ||
| 2000/01 | Runner Up | Kevin Watson | Watson | Kevin | Rotherham United | 46 | 0 | 5 | ||
| 2001/02 | Runner Up | Jamie Cureton | Cureton | Jamie | Reading | 24 | 14 | 15 | ||
| 2001/02 | Runner Up | Kevin Watson | Watson | Kevin | Reading | 12 | 0 | 1 | ||
| 2002/03 | Runner Up | Efetobore Sodje | Sodje | Efetobore | Crewe Alexandra | 23 | 6 | 1 | ||
| 2002/03 | Runner Up | David Wright | Sodje | Efetobore | Crewe Alexandra | 31 | 0 | 1 | ||
| 2003/04 | Winner | Marino Keith | Keith | Marino | Plymouth Argyle | 28 | 12 | 9 | ||
| 2003/04 | Runner Up | Kevin McLeod | McLeod | Kevin | Queens Park Rangers | 26 | 9 | 3 | ||
| 2003/04 | Runner Up | Marcus Bean | McLeod | Kevin | Queens Park Rangers | 23 | 8 | 1 | ||
| 2003/04 | Runner Up | Martin Rowlands | McLeod | Kevin | Queens Park Rangers | 41 | 1 | 10 | ||
| 2003/04 | Runner Up | Tony Thorpe | Thorpe | Tony | Queens Park Rangers | 22 | 9 | 10 | ||
| 2004/05 | Winner | Rowan Vine | Vine | Rowan | Luton Town | 43 | 2 | 9 | ||
| 2005/06 | Winner | Luke Guttridge | Guttridge | Luke | Southend United | 41 | 0 | 5 | ||
| 2005/06 | Winner | Sodje Efe | Efe | Sodje | Southend United | 12 | 1 | 1 | ||
| 2005/06 | Runner Up | Pat Baldwin | Baldwin | Pat | Colchester United | 20 | 5 | 0 | ||
| 2005/06 | Runner Up | Wayne Brown | Brown | Wayne | Colchester United | 38 | 0 | 2 | ||
| 2005/06 | Runner Up | Liam Chilvers | Chilvers | Liam | Colchester United | 33 | 1 | 2 | ||
| 2005/06 | Runner Up | Jamie Cureton | Cureton | Jamie | Colchester United | 7 | 1 | 4 | ||
| 2005/06 | Runner Up | Neil Danns | Danns | Neil | Colchester United | 38 | 3 | 8 | PFA Team of the Year | |
| 2005/06 | Runner Up | Aidan Davison | Davison | Aidan | Colchester United | 41 | 0 | 0 | ||
| 2005/06 | Runner Up | Karl Duguid | Duguid | Karl | Colchester United | 26 | 9 | 0 | ||
| 2005/06 | Runner Up | George Elokobi | Elokobi | George | Colchester United | 10 | 2 | 1 | ||
| 2005/06 | Runner Up | Richard Garcia | Garcia | Richard | Colchester United | 9 | 13 | 5 | ||
| 2005/06 | Runner Up | Dean Gerken | Gerken | Dean | Colchester United | 5 | 2 | 0 | ||
| 2005/06 | Runner Up | Greg Halford | Halford | Greg | Colchester United | 45 | 0 | 7 | ||
| 2005/06 | Runner Up | Chris Iwelumo | Iwelumo | Chris | Colchester United | 46 | 0 | 17 | ||
| 2005/06 | Runner Up | Kemal Izzet | Izzet | Kemal | Colchester United | 19 | 14 | 0 | ||
| 2005/06 | Runner Up | Garry Richards | Richards | Garry | Colchester United | 12 | 3 | 0 | ||
| 2005/06 | Runner Up | Sam Stockley | Stockley | Sam | Colchester United | 21 | 6 | 1 | ||
| 2005/06 | Runner Up | Tony Thorpe | Thorpe | Tony | Colchester United | 5 | 9 | 0 | ||
| 2005/06 | Runner Up | Scott Vernon | Vernon | Scott | Colchester United | 4 | 3 | 1 | ||
| 2005/06 | Runner Up | Kevin Watson | Watson | Kevin | Colchester United | 43 | 1 | 0 | ||
| 2005/06 | Runner Up | John White | White | John | Colchester United | 32 | 3 | 0 | ||
| 2005/06 | Runner Up | Gareth Williams | Williams | Gareth | Colchester United | 6 | 12 | 1 | ||
| 2005/06 | Runner Up | Mark Yeates | Yeates | Mark | Colchester United | 42 | 2 | 5 | ||
| 2006/07 | Runner Up | Brian Wilson | Wilson | Brian | Bristol City | 19 | 0 | 0 | ||
| 2007/08 | Runner Up | Matt Lockwood | Lockwood | Matt | Nottingham Forest | 11 | 0 | 0 | ||
| 2008/09 | Runner Up | Tom Williams | Williams | Tom | Peterborough United | 22 | 3 | 0 | ||
| 2010/11 | Runner Up | Dean Hammond | Hammond | Dean | Southampton | 40 | 1 | 4 | ||
| 2011/12 | Runner Up | Michail Antonio | Hammond | Dean | Sheffield Wednesday | 14 | 0 | 5 | ||
| 2011/12 | Winner | Johnnie Jackson | Hammond | Dean | Charlton Athletic | 35 | 1 | 12 | ||
| 2011/12 | Runner Up | David Prutton | Hammond | Dean | Sheffield Wednesday | 19 | 6 | 2 | ||
| 2011/12 | Runner Up | Danny Batth | Hammond | Dean | Sheffield Wednesday | 44 | 0 | 2 | ||