This film focuses on the disciple of the God of Gamblers, Chow Sing Cho, also known as the “Saint of Gamblers”. A group of people with telekinetic powers matching his attack him and his uncle, accidentally sending him to the year 1937, in Shanghai. This is a year crucial in Sing’s family history, and he must use his powers play a part that has irrevocable effects on his present and future, while trying to find a way back to home, the year 1991.
周星祖（周星驰饰）向赌神拜师已一年，如今自美回港。而之前在赌侠中输给阿星的特功能人士大军为向星报仇，回大陆找师弟们一起对阿星发功，结果发生时空倒流，阿星、大军及三叔（吴孟达饰）均回到1937年的上海。 阿星穿越后先遇上祖父周大福（吴孟达饰），两人投靠上海大亨丁力（吕良伟饰），丁力与阿星的梦中情人如仙（巩俐饰）（台湾版为（方季惟饰））订婚，致阿星失魂落魄。川岛芳子经由丁力的敌人黄金贵之协助欲夺取上海，与丁力相约赌桌上定生死，阿星却在此时失去特异功能令众人忧心不已，原来阿星着迷于仙的低能妹妹如梦（巩俐饰）（台湾版为（方季惟饰）），遂安排如梦与星外出游玩，阿星果然恢复功力。 赌侠Ⅱ之上海滩赌圣 川岛芳子与上海市长、黄金贵等人勾结，如仙发现真相后不幸失足坠楼。市长以如梦代替如仙，引起丁力怀疑。阿星与周大福被川岛芳子抓走，川岛芳子以三叔的性命威胁阿星杀丁力。阿星与丁力串通骗川岛芳子不果，川岛芳子将阿星、周大福、如梦、春天等人囚禁，龙五得知消息后由1991年带领特种部队赶来救援。 赌局上由法国赌神大战上海滩赌圣，两人筋疲力竭将功力用尽，幸得大军暗中援助终保全上海安危，大军并帮助星回到1991年，因无法带如梦同行，阿星的心中无限惆怅。 本片在香港与台湾分别启用不同的女主角，港版为巩俐，台版为方季惟，为这部片增添不少话题，方季惟同时演唱粤语版和国语版插曲。