Sky Bet League Two Player of the Season
| Year | Winner | Club | Second | Third |
|---|---|---|---|---|
| 2063 | Connor May | Hartlepool United | ||
| 2062 | Ola Jones | AFC Wimbledon | ||
| 2061 | Ola Jones | AFC Wimbledon | ||
| 2060 | Aden Betts | Harrogate Town | ||
| 2059 | Abdul Trye | Cardiff City | ||
| 2058 | Craig Casey | Leyton Orient | ||
| 2057 | Brian O'Sullivan | Cheltenham Town | ||
| 2056 | Kevin Griffiths | Birmingham City | ||
| 2055 | Liam Thompson | Burton Albion | ||
| 2054 | Lee Gray | Oldham Athletic | ||
| 2053 | Malcom Strannegård | Bristol Rovers | ||
| 2052 | None | Cheltenham Town | ||
| 2051 | Dele Omotayo | Peterborough United | ||
| 2050 | Mads Spelmann | Wycombe Wanderers | ||
| 2049 | Alex Collicutt | Hartlepool United | ||
| 2048 | Sal Stirman | Accrington Stanley | ||
| 2047 | Kelly Balogun | Barrow AFC | ||
| 2046 | Connor Thomas | Cambridge United | ||
| 2045 | Trent Deen | Bradford City | ||
| 2044 | Chad Hurley | Exeter City | ||
| 2043 | Nicky Bridgwater | Lincoln City | ||
| 2042 | Dom Cowling | Walsall | ||
| 2041 | Simon Raymond | Crawley Town | ||
| 2040 | Simon Raymond | Crawley Town | ||
| 2039 | Thomas McHugh | Tranmere Rovers | ||
| 2038 | Niall Fitzpatrick | Crawley Town | ||
| 2037 | Keith Hegarty | Wrexham | ||
| 2036 | Geraint Perry | Exeter City | ||
| 2035 | Elliott Hooper | Woking | ||
| 2034 | Ashton Missin | Crewe Alexandra | ||
| 2033 | David Thomas | Swindon Town | ||
| 2032 | Benicio Baker-Boaitey | Southend United | ||
| 2031 | Benicio Baker-Boaitey | Southend United | ||
| 2030 | Ellis Chapman | Hartlepool United | ||
| 2029 | Scott Banks | Swindon Town | ||
| 2028 | Pete Colbert | Port Vale | ||
| 2027 | Theo Archibald | Leyton Orient | ||
| 2026 | Mitch Pinnock | Northampton Town | ||
| 2025 | Martyn Waghorn | Forest Green Rovers | ||
| 2024 | Josh Emmanuel | Wrexham | ||
| 2023 | Harry Clifton | Grimsby Town | ||
| 2022 | Kane Wilson | Forest Green Rovers | ||
| 2021 | Paul Mullin | Cambridge United | ||
| 2020 | Eoin Doyle | Swindon Town | ||
| 2019 | James Norwood | Tranmere Rovers | ||
| 2018 | Billy Kee | Accrington Stanley | ||
| 2017 | John Marquis | Doncaster Rovers | ||
| 2016 | Kemar Roofe | Oxford United | ||
| 2015 | Danny Mayor | |||
| 2014 | Gary Roberts | Chesterfield | ||
| 2013 | Tom Pope | Port Vale | ||
| 2012 | Matt Ritchie | Swindon Town | ||
| 2011 | Ryan Lowe | |||
| 2010 | Craig Dawson | Rochdale | ||
| 2009 | Grant Holt | Shrewsbury Town | ||
| 2008 | Keith Andrews | Milton Keynes Dons | ||
| 2007 | Izale McLeod | Milton Keynes Dons | ||
| 2006 | Karl Hawley | Carlisle United |
Most wins
| Ola Jones | 2 |
| Simon Raymond | 2 |
| Benicio Baker-Boaitey | 2 |