Winning Post lets the player take control of a stable of horses, breeding and training them for the ultimate goal, to win the French Grand Prix.

The player can hire breeders, trainers, and jockeys and race in over 240 different races to earn more money. That money can then be used to buy even better personnel and breed faster, stronger horses as well as to keep their horses healthy. Players can also bet on races.

The gameplay consists of choosing options before races, such as choosing which horses to train and what regiment they undertake, viewing stats, hiring personnel, and placing bets. However, the player has no control over races, cannot participate, and is only viewable as a spectator.