Dry made his first class debut for the Free State Cheetahs during the 2009 Currie Cup Premier Division, coming on as a late substitute in their 59–8 victory against Boland Cavaliers in Bloemfontein.

[2] That turned out be his only appearance in the Currie Cup, despite being named on the bench for their matches against the Golden Lions[3] and Western Province.

[4] Dry made a single appearance for university side UFS Shimlas during the 2010 Varsity Cup competition, a 37–31 win over TUT Vikings[5] before joining the Free State Cheetahs' squad for the 2010 Vodacom Cup.

He was also a member of the Blitzbokke that played at the 2013 Rugby World Cup Sevens, but disappointingly got knocked out at the quarter-final stage by Fiji.

Dry once again played in all nine events of the 2013–14 IRB Sevens World Series before participating at the 2014 Commonwealth Games in Glasgow, helping his side all the way to the final, where they got a 17–12 victory over a New Zealand that won the previous four tournaments.