Having moved to England along with his family from South Africa when he was 10 years old, Roy was educated at Whitgift School and represented Surrey in age group cricket from U-11 through to Under-19 and Surrey Academy level. He took part in the Surrey Under-19 tour to South Africa in 2007, where he notably top-scored for Surrey with an innings of 51 in a one-day match against Western Province Under-19s.

He was a member of the 2007 intake of players to the Pemberton Greenish Surrey Academy, and on 15 June 2007 made a decisive contribution on his one-day debut for the Surrey second team, scoring 48 from 33 balls in a Second XI Trophy match against Hampshire which Surrey won by 3 runs.

Roy made no further appearances for the Surrey second team in 2007, but was selected to represent the South at Under-17 level in the ECB Regional Festival, held at Loughborough in July 2007, where he played in three matches.

In the 2008 season, Roy established himself in the Surrey second team. In his debut in the Second XI Championship, Roy scored 88 from 89 balls against a Hampshire attack which included the South African Test match bowler Nantie Hayward, having come to the crease with Surrey in trouble at 89-4.

He made his debut for the Surrey first team in a Twenty20 Cup match against Middlesex on 27 June 2008, and made his List A debut in the Natwest Pro40 League fixture against Yorkshire on 20 July 2008, the day before his 18th birthday.

He was used as a substitute fielder for England's test team against South Africa in the final test of the 2008 series at The Oval.

In September 2008, Roy was selected for the ECB Elite Player Development squad taking part in a triangular tournament against University Sport South Africa and Marylebone Cricket Cl