Donna Crookston was nine years old when she got her first pony. She rode bareback until she talked her parents into buying a saddle when she was 13. As a kid, she showed Western before switching to hunter, jumper, eventing, dressage, and foxhunting. Crookston started driving in June 2002 after she retired. She is a six-time FEI Driving World Championship for Single Horses competitor (2008, 2010, 2012, 2014, 2016, 2018), competing with RG Cowboys Black Cadillac at four consecutive world championships and with Viktor at two consecutive world championships.

In 2022, Crookston and Viktor were fourth at the Live Oak International CAI3*-H1 and the Kentucky Classic CDE CAI3*-H1 before finishing second in the Bromont CAI3*-H1.