Middlesbrough FC Player of the Year Awards 1966 to 2014  
  Year  Winner    Year  Winner   
  1966   Gordon Jones   1990   Not Awarded  
  1967   Not Awarded   1991   Ian Baird  
  1968   Richard Rooks   1992   Not Awarded  
  1969   Richard Rooks   1993   Not Awarded  
  1970   George Smith    1994   Not Awarded  
  1971   Gordon Jones   1995   Not Awarded  
  1972   Jim Platt   1996   Not Awarded  
    Stuart Boam   1997   Juninho Paulista  
  1973   Willie Maddren   1998   Not Awarded  
  1974   Graeme Souness   1999   Hamilton Ricard  
  1975   Not Awarded   2000   Not Awarded  
  1976   Not Awarded   2001   Not Awarded  
  1977   Not Awarded   2002   Gareth Southgate  
  1978   Not Awarded   2003   Not Awarded  
  1979   Stuart Boam   2004   George Boateng  
  1980   David Armstrong   2005   Stewart Downing  
  1981   Jim Platt   2006   Yakubu Aiyegbeni  
  1982   Not Awarded   2007   Jonathan Woodgate  
  1983   Not Awarded   2008   David Wheater  
  1984   Not Awarded   2009   Tuncay Şanlı  
  1985   Tony Mowbray   2010   Barry Robson  
  1986   Tony Mowbray   2011   Joe Bennett  
  1987   Not Awarded   2012   Barry Robson  
  1988   Not Awarded   2013   Grant Leadbitter  
  1989   Not Awarded   2014   George Friend