Kyle May came through the youth system at Carlisle and signed for the club on the 1st of August 2001. Despite featuring in pre season games Kyle has failed to break through to the first team. He had a loan spell at Gretna from the 27th of September. Like so many others Kyle was released by Carlisle United at the end of season, however he was resigned for the 2002/03 season on the 3rd of July 2002. With Roddy Collins return Kyle's chances of first team football were limited, in August he signed a permanent deal with Gretna.
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