Career
Jennings played for local side North Village Rams and had a spell with the Bermuda Hogges in the USL Second Division in 2008. He also played for Royal in the Island Soccer League. He made his debut for Bermuda in a February 2004 friendly match against Trinidad and Tobago and earned a total of 10 caps, scoring 0 goals.
His final international match was an August 2008 CONCACAF Gold Cup qualification match against the Cayman Islands.
