"I Should Have Known Better" was a UK number one single for one week in December 1984 for Jim Diamond. The song was displaced after one week by Frankie Goes to Hollywood's song "The Power of Love". Diamond publicly requested that people not buy his single, but instead buy "Do They Know It's Christmas?"

"I Should Have Known Better" was re-recorded for Diamond's 1993 solo album Jim Diamond. He recorded the song a third time for his 2005 single "Blue Shoes", which also featured a re-recording of "I Won't Let You Down" and covers of old soul songs such as "My Girl".

The song was covered in French by Julie Pietri ("À force de toi"). It was also covered in Italian by Matteo Becucci ("Lo avrei dovuto sapere"), as part of a compilation that showcases the contestants of The X-Factor Italia's second season. The Spanish version of the song "Te Veo Pasar" was covered by Yolandita Monge in her album Luz de Luna.

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