| League Two (Tier Four) Honours | ||||||||||
| Season | Winners/RU | Name | Surname | Chr Name | Club | App | Sub | Goals | Notes | |
| 1959/60 | Runner-Up | Sandy Kennon | Kennon | Sandy | Norwich City | 45 | 0 | 0 | ||
| 1961/62 | Runner-Up | Percy Ames | Ames | Percy | Colchester United | 44 | 0 | 0 | ||
| 1961/62 | Runner-Up | Brian Abrey | Abrey | Brian | Colchester United | 38 | 0 | 1 | ||
| 1961/62 | Runner-Up | Mike Foster | Foster | Mike | Colchester United | 36 | 0 | 8 | ||
| 1961/62 | Runner-Up | John Fowler | Fowler | John | Colchester United | 44 | 0 | 0 | ||
| 1961/62 | Runner-Up | Richie Griffiths | Griffiths | Richie | Colchester United | 16 | 0 | 0 | ||
| 1961/62 | Runner-Up | Trevor Harris | Harris | Trevor | Colchester United | 43 | 0 | 4 | ||
| 1961/62 | Runner-Up | Bobby Hill | Hill | Bobby | Colchester United | 40 | 0 | 3 | ||
| 1961/62 | Runner-Up | Bobby Hunt | Hunt | Bobby | Colchester United | 43 | 0 | 38 | ||
| 1961/62 | Runner-Up | Ronnie Hunt | Hunt | Ronnie | Colchester United | 44 | 0 | 0 | ||
| 1961/62 | Runner-Up | Martyn King | King | Martyn | Colchester United | 43 | 0 | 31 | ||
| 1961/62 | Runner-Up | Tommy Millar | Millar | Tommy | Colchester United | 27 | 0 | 4 | ||
| 1961/62 | Runner-Up | Sammy McLeod | McLeod | Sammy | Colchester United | 12 | 0 | 3 | ||
| 1961/62 | Runner-Up | Peter Wright | Wright | Peter | Colchester United | 44 | 0 | 12 | ||
| 1961/62 | Winner | John Gilchrist | Gilchrist | John | Millwall | 31 | 0 | 0 | ||
| 1961-62 | Runner-Up | Bobby Hill | Hill | Bobby | Colchester United | 40 | - | 3 | ||
| 1963/64 | Winner | Brian Gibbs | Gibbs | Brian | Gillingham | 46 | 0 | 17 | ||
| 1964/65 | Runner-Up | John Gilchrist | Gilchrist | John | Millwall | 29 | 0 | 1 | ||
| 1964/65 | Runner-Up | Ken Jones | Jones | Ken | Millwall | 24 | 0 | 3 | ||
| 1964/65 | Winner | Jimmy Oliver | Oliver | Jimmy | Brighton & Hove Albion | - | - | - | ||
| 1967/68 | Winner | Ray Whittaker | Whittaker | Ray | Luton Town | - | - | - | ||
| 1976/77 | Runner-Up | Bobby Hodge | Hodge | Bobby | Exeter City | - | - | - | ||
| 1977/78 | Runner-Up | Tony Hadley | Hadley | Tony | Southend United | - | - | - | ||
| 1977/78 | Winner | Roger Joslyn | Joslyn | Roger | Watford | 43 | 0 | 4 | ||
| 1978/79 | Winner | Steve Hetzke | Hetzke | Steve | Reading | - | - | - | ||
| 1978/79 | Winner | Ian Atkins | Atkins | Ian | Shrewsbury Town | - | - | - | ||
| 1979/80 | Runner-Up | Ron Green | Green | Ron | Walsall | - | - | - | ||
| 1979/80 | Runner-Up | Roy McDonough | McDonough | Roy | Walsall | - | - | - | ||
| 1981/82 | Winner | Stewart Houston | Houston | Stewart | Sheffield United | - | - | - | ||
| 1982/83 | Runner-Up | Les Mutrie | Mutrie | Les | Hull City | - | - | - | ||
| 1984/85 | Runner-Up | Steve Hetzke | Hetzke | Steve | Blackpool | 30 | 0 | 5 | ||
| 1985/86 | Winner | Paul Roberts | Roberts | Paul | Swindon Town | 25 | 2 | 0 | ||
| 1986/87 | Winner | Warren Donald | Donald | Warren | Northampton Town | - | - | - | ||
| 1986/87 | Winner | Warren Donald | Donald | Warren | Northampton Town | - | - | - | ||
| 1987/88 | Winner | Steve Mardenborough | Mardenborough | Steve | Cardiff City | - | - | - | ||
| 1990/91 | Winner | Steve Mardenborough | Mardenborough | Steve | Darlington | - | - | - | ||
| 1991/92 | Winner | Andy Farrell | Farrell | Andy | Burnley | - | - | - | ||
| 1994/95 | Runner-Up | Jimmy Walker | Walker | Jimmy | Walsall | - | - | - | ||
| 1994/95 | Winner | Warren Aspinall | Aspinall | Warren | Carlisle United | 44 | 0 | 6 | ||
| 1995/96 | Runner-Up | Dave Martin | Martin | Dave | Gillingham | 27 | 4 | 0 | ||
| 1995/96 | Winner | John Vaughan | Vaughan | John | Preston North End | - | - | - | ||
| 1996/97 | Runner-Up | Mark Blake | Blake | Mark | Fulham | 36 | 1 | 7 | ||
| 1996/97 | Winner | Gavin Johnson | Johnson | Gavin | Wigan Athletic | 33 | 0 | 3 | ||
| 1997/98 | Runner-Up | Sodje Efe | Efe | Sodje | Macclesfield Town | 41 | 0 | 3 | ||
| 1997/98 | Winner | Sean Farrell | Farrell | Sean | Notts County | 32 | 3 | 15 | ||
| 1998/99 | Runner-Up | John Taylor | Taylor | John | Cambridge United | 29 | 11 | 17 | ||
| 1998/99 | Winner | Kevin Rapley | Rapley | Kevin | Brentford | 3 | 9 | 3 | ||
| 1998/99 | Winner | Martin Rowlands | Rapley | Kevin | Brentford | 32 | 4 | 4 | ||
| 1998/99 | Winner | Andy Woodman | Woodman | Andy | Brentford | 22 | 0 | 0 | ||
| 1999/2000 | Runner-Up | Guy Branston | Branston | Guy | Rotherham United | 30 | 0 | 4 | ||
| 1999/2000 | Runner-Up | Kevin Watson | Watson | Kevin | Rotherham United | 44 | 0 | 1 | ||
| 2001/02 | Runner-Up | Aaron Skelton | Skelton | Aaron | Luton Town | 9 | 0 | 1 | ||
| 2001/02 | Winner | Marino Keith | Keith | Marino | Plymouth Argyle | 13 | 10 | 9 | ||
| 2005/06 | Runner-Up | Scott McGleish | McGleish | Scott | Northampton Town | 39 | 3 | 17 | ||
| 2005/06 | Winner | Simon Hackney | Hackney | Simon | Carlisle United | 9 | 21 | 6 | ||
| 2005/06 | Winner | Gavin Johnson | Johnson | Gavin | Northampton Town | 22 | 2 | 1 | ||
| 2007/08 | Runner-Up | Tom Williams | Williams | Tom | Peterborough United | 3 | 4 | 0 | ||
| 2008/09 | Winner | Marcus Bean | Halls | John | Brentford | 43 | 1 | 9 | ||
| 2008/09 | Winner | John Halls | Halls | John | Brentford | 22 | 1 | 0 | ||
| 2008/09 | Winner | Charlie MacDonald | MacDonald | Charlie | Brentford | 38 | 0 | 16 | ||
| 2009/10 | Winner | Mike Edwards | Edwards | Mike | Notts County | 37 | 3 | 5 | ||
| 2009/10 | Winner | Stephen Hunt | Hunt | Stephen | Notts County | 32 | 0 | 1 | ||
| 2010/11 | Runner-Up | Efetobore Sodje | Sodje | Efetobore | Bury | 40 | 0 | 3 | ||
| 2010/11 | Winner | Dean Morgan | Morgan | Dean | Chesterfield | 18 | 3 | 1 | ||