| Tottenham Hotspur Player of the Year Awards 1987 to 2018 | ||||||||
| Year | Winner | Year | Winner | |||||
| 1987 | Gary Mabbutt | 2004 | Jermain Defoe | |||||
| 1988 | Chris Waddle | 2005 | No Award (Annual to Seasonal) | |||||
| 1989 | Erik Thorstvedt | 2006 | Robbie Keane | |||||
| 1990 | Paul Gascoigne | 2007 | Dimitar Berbatov | |||||
| 1991 | Paul Allen | 2008 | Robbie Keane | |||||
| 1992 | Gary Lineker | 2009 | Aaron Lennon | |||||
| 1993 | Darren Anderton | 2010 | Michael Dawson | |||||
| 1994 | Jurgen Klinsmann | 2011 | Luka Modric | |||||
| 1995 | Teddy Sheringham | 2012 | Scott Parker | |||||
| 1996 | Sol Campbell | 2013 | Gareth Bale | |||||
| 1997 | Sol Campbell | 2014 | Christian Eriksen | |||||
| 1998 | David Ginola | 2015 | Harry Kane | |||||
| 1999 | Stephen Carr | 2016 | Toby Alderweireld | |||||
| 2000 | Stephen Carr | 2017 | Christian Eriksen | |||||
| 2001 | Neil Sullivan | 2018 | Jan Vertonghen | |||||
| 2002 | Simon Davies | 2019 | ||||||
| 2003 | Robbie Keane | 2020 | ||||||