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Middlesbrough Player of the Year Award Winners from 1966 to 2019
This is a list of Middlesbrough Player of the Year from 1969 till 2019. Middlesbrough Player of the Season is voted by Middlesbrough club supporters.
Year Winner 1966 
Gordon Jones 1967 Not Awarded 1968
Dickie Rooks 1969
Dickie Rooks 1970
George Smith 1971
Gordon Jones 1972 
Jim Platt
Stuart Boam 1973
Willie Maddren 1974 
Graeme Souness 1975 Not Awarded 1976 Not Awarded 1977 Not Awarded 1978
Stan Cummins 1979
Stuart Boam 1980
David Armstrong 1981
Jim Platt 1982 Not Awarded 1983 Not Awarded 1984 Not Awarded 1985
Tony Mowbray 1986
Tony Mowbray 1987 Not Awarded 1988 Not Awarded 1989 Not Awarded 1990 Not Awarded 1991
Ian Baird 1992 Not Awarded 1993 Not Awarded 1994 Not Awarded 1995 Not Awarded 1996 Not Awarded 1997 
Juninho Paulista 1998 Not Awarded 1999 
Hamilton Ricard 2000 Not Awarded 2001 Not Awarded 2002
Gareth Southgate 2003 Not Awarded 2004 
George Boateng 2005
Stewart Downing 2006 
Yakubu Aiyegbeni 2007
Jonathan Woodgate 2008
David Wheater 2009 
Tuncay Şanlı 2010
Barry Robson 2011
Joe Bennett 2012
Barry Robson 2013
Grant Leadbitter 2014
George Friend 2015
George Friend 2016
Adam Clayton 2017
Ben Gibson 2018 
Adama Traoré 2019 
Darren Randolph 2020
| Year | Winner | |
| 1966 |
| Gordon Jones |
| 1967 | Not Awarded | |
| 1968 |
| Dickie Rooks |
| 1969 |
| Dickie Rooks |
| 1970 |
| George Smith |
| 1971 |
| Gordon Jones |
| 1972 |
| Jim Platt |
| Stuart Boam | |
| 1973 |
| Willie Maddren |
| 1974 |
| Graeme Souness |
| 1975 | Not Awarded | |
| 1976 | Not Awarded | |
| 1977 | Not Awarded | |
| 1978 |
| Stan Cummins |
| 1979 |
| Stuart Boam |
| 1980 |
| David Armstrong |
| 1981 |
| Jim Platt |
| 1982 | Not Awarded | |
| 1983 | Not Awarded | |
| 1984 | Not Awarded | |
| 1985 |
| Tony Mowbray |
| 1986 |
| Tony Mowbray |
| 1987 | Not Awarded | |
| 1988 | Not Awarded | |
| 1989 | Not Awarded | |
| 1990 | Not Awarded | |
| 1991 |
| Ian Baird |
| 1992 | Not Awarded | |
| 1993 | Not Awarded | |
| 1994 | Not Awarded | |
| 1995 | Not Awarded | |
| 1996 | Not Awarded | |
| 1997 |
| Juninho Paulista |
| 1998 | Not Awarded | |
| 1999 |
| Hamilton Ricard |
| 2000 | Not Awarded | |
| 2001 | Not Awarded | |
| 2002 |
| Gareth Southgate |
| 2003 | Not Awarded | |
| 2004 |
| George Boateng |
| 2005 |
| Stewart Downing |
| 2006 |
| Yakubu Aiyegbeni |
| 2007 |
| Jonathan Woodgate |
| 2008 |
| David Wheater |
| 2009 |
| Tuncay Şanlı |
| 2010 |
| Barry Robson |
| 2011 |
| Joe Bennett |
| 2012 |
| Barry Robson |
| 2013 |
| Grant Leadbitter |
| 2014 |
| George Friend |
| 2015 |
| George Friend |
| 2016 |
| Adam Clayton |
| 2017 |
| Ben Gibson |
| 2018 |
| Adama Traoré |
| 2019 |
| Darren Randolph |
| 2020 | ||
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