Career
He played professionally for Lincoln City but having dropped out of league football he has had numerous short stints with clubs in the Midlands without finding a regular home. May begin his career in the academy at Coventry City, joining Tamworth on a work-experience basis toward the end of the 2002-2003 season. He signed for Lincoln City in the summer of 2003.
In March 2004 he joined Halifax Town on a loan basis.
Following his release by Lincoln, May rejoined Tamworth. He struggled to make an impression with Tamwort and was loaned out to Moor Green in September 2004 and Redditch United in November 2004.
He made an immediate impression, scoring twice on his debut against Merthyr Tydfil in the FA Trophy but ran into problems when he turned up late for the following weeks fixture against Sutton Coldfield Town. He returned to Tamworth, having his contract terminated in December 2004.
Although he was offered a deal by Bromsgrove Rovers, he spent four months out of football before rejoining Redditch United.
He commenced the season at Sutton Coldfield but was on the move again in November 2005, linking up with Stourport Swifts. He joined Solihull Borough for the 2006–2007 season scoring 30 goals in 39 appearances, moving on to Brackley Town in February 2007 before rejoining Solihull a little over a month later. May began the season with Stratford Town, scoring 16 league goals in just 21 appearances.
Having impressed against them in an tie earlier in the season, May joined up with Hednesford Town in January 2008 with Hednesford manager Philosophy Starbuck stating that "I"ve bought Rory in to give us more of a physical presence up front, it will help stop the ball coming straight back as it causes problems for the defence." In April 2008, May was on the move again, joining Worcester City on loan for the remainder of the season.
Foreign the 08–09 season May joined Willenhall Town in the Northern Premier League Division 1 South.