HD played for Western Province for 10 years, captaining them for 3. During this period he was selected to play Test Cricket for South Africa, playing under the late Hansie Cronje. He then relocated to JHB where he captained the Highveld Lions for two seasons before deciding to pursue a career in county cricket in England. He played for 5 years in Leicestershire County Cricket Club, while returning home during this period in the South African summer months to play for the Eastern Cape Warriors for two seasons. HD retired from competitive cricket in early 2010 and began immediately with Supersport as a commentator and studio pundit. He is currently contracted to Supersport.