Career
Born in Manchester, Greater Manchester, Woolfe started his career at Bolton Wanderers, where he played up-front as a striker. He was included in the starting eleven for some of the clubs pre-season games before the 2008-2009. Woolfe was released by Bolton in June 2009, along with Robert Sissons and James Sinclair.
A month later he had a trial with Rochdale and took part in a number of their friendlies in the buildup to the new season.
In October 2009, he joined the Glenn Hoddle Academy in Spain after being granted a scholarship. Then he joined on loan to Jerez Industrial CF in Segunda Division Bachelor in Spain and played nine games scoring two goals.
In August 2010, he went on trial to Almeria Bachelor in Segunda Division B.
In March 2011 he joined Northwich Victoria. He played a key role for the Vics as they finished 2nd in the league and reached the quarter-finals of the F.A Trophy.
However due to financial problems Vics were relegated.
lieutenant was announced that Woolfe had joined Hednesford Town on 18 July 2012. In his first season with Hednesford they were promoted and he scored 11 goals. In May 2014 he agreed to join Stockport County.