Woolfe joined The Nomads in January 2016 having started his career at Bolton Wanderers where he played up front as a striker, making his debut as a second half substitute against Sporting Lisbon in the second leg of the UEFA Cup in 2007. In 2008, Woolfe joined Wrexham on loan for a brief spell, before heading to Spanish Segunda Division B side, Jerez Industrial where he scored 2 goals in 10 appearances.
Since then, Woolfe spent a successful spell an Northwich Victoria, helping the side to second place in the league and the quarter finals of the FA Trophy. In May 2014, Woolfe then joined Stockport County, making 20 appearance in the Conference North.
Woolfe made his debut for The Nomads in a 2-0 victory over TNS in January 2016. He went on to make 81 starts in all competitions as well as 40 substitute appearances. Woolfe was named as a substitute in the 2016/17 Welsh Premier League Team of the Season as chosen by Managers of the opposing WPL sides and won the Welsh Cup in 2018.