De Silva is a product of the Crystal Palace academy and possesses pace and quick feet. He made his début in the FA Cup against Derby County on 7 January 2012 and made his league début away to Blackpool on 21 January 2012. In May 2012, he signed a three-year contract with Palace. In the 2012/13 season, Kyle De Silva suffered a series of injuries which kept him out of action for half a year. On 22 March 2013 he signed for Barnet on loan until the end of the season. He made his debut as a 66th minute substitute for Luke Gambin in a 0-0 home draw with Cheltenham Town.