[4] He joined Halifax Town on loan in October 2000 for three months and then returned to Darlington on a permanent transfer for a fee of £50,000 in August 2001,[4] where he made over 270 appearances in all competitions and was the club's player of the year in the 2006–07 season, but after making only six first-team appearances for Darlington at the start of the 2007–08 season he joined Shrewsbury Town on a one-month loan in October 2007.
[7] Following Darlington's failure to gain promotion from Football League Two in the 2007–08 season, Wainwright was one of several players surprisingly released by the club in May 2008.
[8] He joined Morecambe in June 2008 and excelled in a left wing-back role before his season was cut short by an achilles injury.
[10] On 28 February 2012, Wainwright re-signed for former club Darlington,[11] who were in severe financial straits and battling relegation from the Conference National following a 10-point deduction for entering administration in December 2011.
Wainwright made his second Darlington debut on 3 March 2012, in a 0–1 home loss to Stockport County; he wore the number 26 shirt and was replaced by Clark Keltie in the 67th minute.