1. Jerome Sinclair - 16 years and 6 days
In 2012, Sinclair set the record for Liverpool as the youngest player ever to play for the club. He came on as a substitute against his former academy club, West Brom, in the EFL Cup. Sinclair would go on to make only four more appearances for the club.
Unfortunately, at 27, football as a professional career did not work out for Sinclair. The striker eventually moved to Watford and subsequently had loans down the EFL ladder before playing his last professional season with CSKA Sofia in Bulgaria. A couple of years ago, he trained with Oxford United but ultimately did not sign. He now owns a fried chicken restaurant in Birmingham.