Season 1 of Who's The Winner premiered on September 2, 1991.

Shek Chi Hong is an honest and kind person. To earn a living, Chi Hong aspires to be a chef in Man Long’s casino but he ends up becoming a dealer instead. After witnessing his teacher's death, he is more determined not to take up gambling. But somehow, he has no choice but to learn the gambling skills as it is part of the nature of his work. He goes through many turbulence in his life, losing many friends and comrades as well as love.

Season 2 of Who's The Winner premiered on October 5, 1992.

Shek Chi Hong is now the number one "God of Gamblers" in the gambling world. He is a genius in gambling but prefers a quiet life. However, he can’t change his own destiny as long as he hasn’t retired from the gambling world. Knowing that Hung Fung's gambling skills have improved tremendously over the years, Cheung Tin Jing resorts to inviting Chi Hong to help him. Chi Hong refuses to step into the gambling world again due to the promise to his wife. It is not until Cheung Tin Jing fakes a heart attack that Ah Kong decides to help him finally. There, he meets Cheung Tin Jing's only daughter, Cheung Sik Yu and her childhood friend, Dik San. However, after his helping in Tin Ding winning over Mun Long, this in turn causes his wife's death. Since then, he becomes disillusioned in life.

Season 3 of Who's The Winner premiered on November 15, 1993.

Ching Yat Fung is a loyal friend and regards friendship important. He is the top gambler that all renounce to with. Many call him the evil gambler but he is kind at heart. Many people eyes his no.1 spot as the King of Gamblers. 5 years ago, Yik Fung’s family is attacked. He is saved by his servant’s son and good friend, Yik Tin Yeung. The life and friendship of Yat Fung and Tin Yeung is a rocky one, forming lies, deceit, and hatred, and in the end they must battle against each other for the number one spot.

Season 4 of Who's The Winner premiered on September 13, 2010.