Lawless scored against Championship team Derby County with a "superb finish past Carroll from a tight angle" after evading the opponent defence in an FA Cup third round tie on 3 January 2009, which put Forest Green 2–0 up, although they went on to lose 4–3. He missed Forest Green's FA Trophy tie against Redditch United because of a hamstring injury, as well as the semi-final of the Conference League Cup against Woking. He made his return in a 2–1 defeat to Eastbourne Borough on 17 January 2009 and was substituted in the 64th minute as a precaution. After missing the match against Histon because of a one-match suspension, Lawless contributed with an assist and a goal on his return against Northwich on 18 February 2009, after heading from a corner kick for John Hardiker to score and himself finishing with a goal from close range. He was forced to miss games against Cambridge United and Kidderminster in April 2009 due to a stomach illness, and he made his return in the 2009 Conference League Cup Final, which was lost 3–0 to A.F.C. Telford United on a penalty shoot-out, after a 0–0 extra time draw. His season ended prematurely after he suffered a broken leg against York City following a heavy challenge on 21 April 2009, with an X-ray confirming his fibula endured a hairline fracture. He completed the season with 39 appearances and six goals and Harvey hoped his budget would allow for Lawless to stay at the club.
Lawless signed for Forest Green's Conference Premier rivals York City on a one-year contract on 17 June 2009, despite there being two Football League clubs looking to sign him. He made his debut in a 2–1 defeat to Oxford United on 8 August 2009. After suffering from a virus he was forced to miss a game against Cambridge United in September 2009, and he recovered ahead of York's game against Kidderminster. He scored his first goal for York with the only goal in a 1–0 victory over Gateshead on 24 November 2009. He pulled his hamstring in a 1–0 defeat to Eastbourne on 27 February 2010 and made his return as a 64th-minute substitute in a 4–0 victory at Grays Athletic on 30 March. He played in both legs of York's play-off semi-final victory over Luton Town, which finished 2–0 on aggregate. He started in the 2010 Conference Premier play-off Final at Wembley Stadium on 16 May, which York lost 3–1 to Oxford. He finished the season with 45 appearances and one goal for York.
After joining York City in 2009, Lawless moved into a house with teammates Neil Barrett, James Meredith, Richard Pacquette and Daniel Parslow. He has an interest in art, which he studied as a GCSE, saying "I wouldn't mind trying to make a living from it one day but my main priority is football". He is a Manchester United supporter and attention to his interest in art was first drawn after producing a painting of manager Alex Ferguson.