 At the age of 15, Kelly joined Oakham School in England on a sports scholarship in 2003 and represented the cricket first XI for three seasons.At the end of his lower sixth year in 2006, he interrupted his A-level studies to concentrate on playing for Bermuda in their preparations for the 2007 Cricket World Cup.Having been selected in Bermuda's final 15-man World Cup squad, he will returned to the school only after the completion of the tournament.