[1] He did not make his first-class debut for the Leewards until the 1999–2000 season,[2] replacing usual keeper Ridley Jacobs, who was on tour with the West Indies at the time.
[6] However, Simmonds played only two matches in each of the two following seasons, with Jason Williams increasingly favoured when Jacobs was on international duty.
[7] Nevis won its first two matches to progress to the semi-final round, and against Trinidad and Tobago, Simmonds top-scored with 65 not out from 47 balls, an innings which included three sixes.
[8] Partially based on this form, Simmonds was selected to keep wicket for the Leewards in the 2007–08 KFC Cup, playing the only three List A matches of his career.
[12] In August 2011, Simmonds was shot during an attempted robbery at a house in Pond Hill, where he had been engaged in illegal gambling.