Some movie posters for this film featured a long text preamble that read: "Haven't you ever done something in your life you wish you could do over again... and this time do it right! After fourteen years, Jack finally has a chance to replay the worst moment of his life. But first, he has to convince Reno that history won't repeat itself".
Kirk Cameron plays Teddy Hightower, Reno and Gigi's son. Tracey Gold plays an unnamed friend of Jack and Holly's daughter Jaki Dundee. By the time this movie was released, Cameron and Gold were playing brother and sister in the TV sitcom Growing Pains (1985).
Though Hightower and Dundee's alma mater is universally referred to by the characters as "Taft", logos, signage and lettermen's jackets in the film identify it as (the fictional) Midway Union High School.
Herman Edwards who is an extra in this film is a former NFL head coach as well as a former defensive back. Edwards is famous for scoring the touchdown against the NY Giants in what is famously called The Miracle of the Meadowlands.
The trivia item below may give away important plot points.
The film's title can be interpreted as being a reference to the opening line of Charles Dickens' 'A Tale of Two Cities', "It was the best of times, it was the worst of times", as the film is about "the worst of times" (the loss of a football match) and "the best of times" (winning a replay rematch about a decade later).