Jack Wilkinson made a very promising start to his Pools career when, still a member of the youth team, he scored on his league debut against Rushden & Diamonds in November 2003. He followed that up with a wonderful chip against Swindon two weeks later but the form of Eifion Williams and Joel Porter kept Wilkinson out of the side for a remainder of the season. Injury interrupted the following season and Wilkinson watched as fellow youngsters David Foley and Andy Appleby moved ahead of him in the queue behind first-team regulars Porter and Adam Boyd.
Wilkinson signed his first professional contract in 2005, but failed to force his way back into the first team picture. He was released in May 2006.