Sky Bet League Two Manager of the Season
| Year | Winner | Club | Second | Third |
|---|---|---|---|---|
| 2063 | Aaron Slattery | Hartlepool United | ||
| 2062 | Jamie Gilbert | Cambridge United | ||
| 2061 | Harvey Swann | Southend United | ||
| 2060 | James Rennie | Oldham Athletic | ||
| 2059 | Keelan Fulloway | Bradford City | ||
| 2058 | Jonny Bannister | Accrington Stanley | ||
| 2057 | Manuel Santos | Exeter City | ||
| 2056 | Andy Breuer | Carlisle United | ||
| 2055 | Mike Wadsworth | Oldham Athletic | ||
| 2054 | Jonny Bannister | Preston North End | ||
| 2053 | Conner Bathgate | Accrington Stanley | ||
| 2052 | Alex White | Southend United | ||
| 2051 | Luis Stirling | Crawley Town | ||
| 2050 | Laurenţiu Brănescu | Swindon Town | ||
| 2049 | Mackenzie Carney | Southend United | ||
| 2048 | Scott Hogan | Birmingham City | ||
| 2047 | Jonny Bannister | Oxford United | ||
| 2046 | Scott Hogan | Tranmere Rovers | ||
| 2045 | James Bradley | Walsall | ||
| 2044 | Jay Biggs | Hartlepool United | ||
| 2043 | Wes Harding | Woking | ||
| 2042 | Ryan Sessegnon | AFC Fylde | ||
| 2041 | Ryan Moore | Bolton Wanderers | ||
| 2040 | Jamie Cunningham | Bradford City | ||
| 2039 | Jordan Cousins | Oxford United | ||
| 2038 | Nicky Cowley | Carlisle United | ||
| 2037 | Jon Brady | Mansfield Town | ||
| 2036 | Alex Baptiste | Cambridge United | ||
| 2035 | Alfie Doughty | Hartlepool United | ||
| 2034 | Darren Charles | Bristol Rovers | ||
| 2033 | Chuba Akpom | Cambridge United | ||
| 2032 | Shane Duffy | Wrexham | ||
| 2031 | Simon Weaver | Wycombe Wanderers | ||
| 2030 | Johnnie Jackson | Carlisle United | ||
| 2029 | Martin Paterson | Bradford City | ||
| 2028 | Paul Cook | Chesterfield | ||
| 2027 | Michael Flynn | Walsall | ||
| 2026 | Paul Ince | Doncaster Rovers | ||
| 2025 | Jonathan Hogg | Forest Green Rovers | ||
| 2024 | Harry Watling | Exeter City | ||
| 2023 | Jon Brady | Northampton Town | ||
| 2022 | Rob Edwards | Forest Green Rovers | ||
| 2021 | Michael Duff | Cheltenham Town | ||
| 2020 | David Artell | Crewe Alexandra | ||
| 2019 | Danny Cowley | Lincoln City | ||
| 2018 | John Coleman | Accrington Stanley | ||
| 2017 | Darren Ferguson | Doncaster Rovers | ||
| 2016 | Chris Wilder | Northampton Town | ||
| 2015 | Gareth Ainsworth | Wycombe Wanderers | ||
| 2014 | Russ Wilcox | Scunthorpe United | ||
| 2013 | Martin Allen | Gillingham | ||
| 2012 | Paolo di Canio | Swindon Town | ||
| 2011 | John Sheridan | Chesterfield | ||
| 2010 | Keith Hill | Rochdale | ||
| 2009 | Paul Tisdale | Exeter City | ||
| 2008 | Graham Turner | |||
| 2007 | Danny Wilson | Hartlepool United | ||
| 2006 | Paul Simpson | Carlisle United | ||
| 2005 | Steve Tilson | Southend United | ||
| 2004 | Dave Penney | Doncaster Rovers | ||
| 2003 | Denis Smith | Wrexham | ||
| 2002 | Paul Sturrock | Plymouth Argyle | ||
| 2001 | Micky Adams | Brighton and Hove Albion | ||
| 2000 | John Hollins | Swansea City | ||
| 1999 | Ray Graydon | Walsall |
Most wins
| Jonny Bannister | 3 |
| Scott Hogan | 2 |
| Jon Brady | 2 |