Darragh began competing at age 10. He was born and raised on a farm and his parents are both trainers.
He got his start in the United States and showed horses for clients at North Run stable in Wellington, FL, United States. But in September 2012 he broke off to form Oakland Ventures, LLC. "For me, North Run was like going to college; you do four years of college and you learn so much. It was just time for me to try and do something on my own and make a go of it."
Darragh's ambition is to compete in the Olympics.
4th place on Balou du Reventon - CSI 4* Longines Trophy Grand Prix of Maastricht
1st place on Carlson 93 - Prijs Ifor Williams CSI 3* Grand Prix
4th place on Cassini Z - International Jumping CSI 5* Oslo Grand Prix
1st place on Balou du Reventon - Barcelona CSIO5* Longines FEI Jumping Nations Cup Final
2nd place on Extra Van Essene - CSIO5* Negrita Cup
1st place on Cassini Z - CSIO5* Dublin Stakes
1st place- 2015 Nations Cup CSIO 5* in Dublin
Competed in the 2010 FEI World Cup Final
Competed in the 2014 World Championships
2015 LGCT Paris Grand Prix Bronze medallist with Sans Soucis Z