Central defender Jake Osborne was in the Norwich City Under 15 squad that won the Northern Ireland Milk Cup in August 2001. He is the brother of goalkeeper Aaron, Jake made his Under-19 debut against Crystal Palace, and scored in the FA Youth Cup victory over Wimbledon.

A former student of Cromer High School, Jake was offered a place as a scholar at Norwich's academy in January 2003. He accepted and became a full time scholar in July 2003. Sammy Morgan described him in the summer of 2003 as "very strong and an excellent competitor with a first class attitude."