Ray Winninger is a game designer who has worked on a number of roleplaying games, including the Dungeons & Dragons fantasy roleplaying game. He is the former Executive Producer for the Wizards of the Coast Dungeons & Dragons studio.

Ray Winninger was a competitive chess player as a child, and at age nine he discovered Avalon Hill games and Dungeons & Dragons while looking for chess opponents at a local hobby shop/game store.^[1] He designed his first game as "a futuristic man-to-man miniatures system", and by age fourteen he had designed an enormous campaign world for the Dungeons & Dragons game system.^[1] His first published work was an adventure called Countdown! for FASA's Doctor Who role-playing game.^[1] He worked for TSR, including work on Dungeons & Dragons, throughout the 1980s and early 1990s.^[1]

Winninger was the co-designer of DC Heroes and Torg.^[2] He then worked on staff at Mayfair Games, and became Editorial Director for Mayfair after Chill was released.^[3]: 168 He brought back the Role Aids line, intending to recreate it with more sophisticated material for AD&D than that which TSR was producing at the time.^[3]: 168 Winninger designed the Underground (1993) role-playing game for Mayfair Games.^[3]: 169 Underground was set in the year 2021 and "allowed players to assume the roles of superhuman, genetically enhanced soldiers fighting a patriotic war to take their society back from a corrupt government"; when Mayfair Games withdrew much of its support of the game despite its popularity, Winninger moved onto other projects.^[1] Mayfair also intended to produce a game called D.O.A. by Greg Gorden with major contributions by Winninger, but the game was never published.^[3]: 170 He worked for Dragon magazine, first taking over the "RPG reviews" column from Chris Pramas, before moving on to "Dungeoncraft", a column for guiding Dungeon Masters to create their own campaign worlds.^[1] He also worked as a contributing editor of Dragon magazine.^[2]

Winninger later became a senior platform strategist at Microsoft.^[2]

In 2020, Winninger became the Executive Producer in charge of the Dungeons & Dragons studio at Wizards of the Coast replacing Mike Mearls, the previous Dungeons & Dragons design team head.^[4][5][6] In October 2022, Winninger announced that he had left Wizards of the Coast.^[7]

Ray Winninger has worked for TSR, West End Games, Mayfair Games, Last Unicorn Games, and Pulsar Games. His "Dungeoncraft" column ran in Dragon from 1999-2002, during which time he also served as a contributing editor to the magazine.

He was the executive producer for Harebrained Schemes' 2014 Miniature wargaming game Golem Arcana.^[8]