Leading Jockey '99 is the sequel to Leading Jockey Highbredd and is too a horse racing game. The game begins too choosing 2 horses to breed and create a proper racing horse that will be born of the union of those 2 horses.

In the game the player can compete in differents tracks and in a variety of weather conditions like sun, cloudy or rain. The gameplay is really arcade since to gain speed the player has to press the Circle Button lots of time, but it also has to be careful not to tire so much his horse or the horse stamina will be over, and reduce to speed at the end of the race, so is better to be in the group and accelerate in the last part of the race to have some chances of win.