Most Premier League winner's medals: 13, Ryan Giggs (1992–93, 1993–94, 1995–96, 1996–97, 1998–99, 1999–2000, 2000–01, 2002–03, 2006–07, 2007–08, 2008–09, 2010–11, 2012–13)[1] Most Player of the Season awards: 2[15] Thierry Henry (2003–04 and 2005–06) Cristiano Ronaldo (2006–07 and 2007–08) Nemanja Vidić (2008–09 and 2010–11) Most Player of the Month awards: 7[15] Sergio Agüero (October 2013, November 2014, January 2016, April 2016, January 2018, February 2019, January 2020)[138]