Winston, who will become a free agent on Wednesday, was unopposed in the voting.
"It is my honor to continue my service as president of our union," Winston said. "I am grateful to the board of player reps for believing in me and will keep fighting for every NFL player during this important time in our history."
The executive board also elected New York Giants linebacker Mark Herzlich as the union's treasurer.
The four new player members of the executive committee are Sam Acho of the Chicago Bears, Thomas Morstead and Michael Thomas of the New Orleans Saints, and Russell Okung of the San Diego Chargers. They replace Matt Hasselbeck, Shaun Suisham and Ryan Wendell.
Returning as board members are Lorenzo Alexander of the Buffalo Bills, Zak DeOssie of the Giants, Richard Sherman of the San Francisco 49ers, Adam Vinatieri of the Indianapolis Colts and Benjamin Watson of the Baltimore Ravens.
"This union has always relied on the strength and solidarity of its player leaders," NFLPA executive director DeMaurice Smith said in a statement. "I want to thank those who have served, appreciate the ongoing commitment of our returning members and welcome the new members of our executive committee."