Mister Winner is a sitcom about a well-meaning but hapless chap who is prone to accidents, complications and landing himself in unusual and often somewhat dangerous situations.

Leslie plans to propose to his girlfriend, Jemma Smith, but unknown to him, she is having doubts about their relationship as he doesn't take life seriously enough. Jemma is a young professional from Croydon who loves Leslie, but doesn't know if that's enough as he doesn't have a job, any money, or ever take her anywhere. But he makes her laugh more than anyone else ever has.