Players who have won the Premier League Player of the Season award the most times

Since the 1994–95 season, the Premier League Player of the Season award has been given to the best player of each season in the Premier League. In the history of the Premier League, only four players have won the Premier League Player of the Season award twice. Manchester City’s Belgian attacking midfielder Kevin De Bruyne, who most recently won the Premier League Player of the Season award, is a two-time Premier League Player of the Season award winner. Kevin De Bruyne won the Premier League Player of the Season award for the first time in the 2019-20 season.

Former Manchester United defender Nemanja Vidic is another player who has won the Premier League Player of the Season award twice. Serbian defender Nemanja Vidic won the Premier League Player of the Season award for the first time in the 2008–09 season. Manchester United also became Premier League champions that season. Later, Nemanja Vidic was named Premier League Player of the Season in the 2010–11 season when Manchester United became Premier League champions. With this, Nemanja Vidic has also become the defender who has been selected as the Premier League Player of the Season the most times.

Former Manchester United forward Cristiano Ronaldo is another player who has won the Premier League Player of the Season award twice. Portuguese forward Cristiano Ronaldo was named Player of the Season by Manchester United during the 2006–07 and 2007–08 Premier League seasons. Cristiano Ronaldo is the first Portuguese player to be selected as the Premier League Player of the Season.

Former Arsenal forward Thierry Henry is the first person to win the Premier League Player of the Season award twice. Thierry Henry was named Premier League Player of the Season for the first time during Arsenal’s 2003–04 Premier League Champions. Afterwards, Thierry Henry was named Premier League Player of the Season for the 2005–06 season as well. Arsenal finished fourth that season. Regardless, Arsenal’s French legend Thierry Henry is the first player to win the Premier League Player of the Season award twice.