Darragh, the son of two trainers, began his show jumping career at age 10 in Offaly, Ireland. By 14, he was competing in his first grand prix, and at 19, he earned a training bursary at the prestigious Dublin Horse Show to work with a top American coach.

Shortly thereafter, Darragh joined North Run Farm, training under Missy Clark and John Brennan. With their guidance, he partnered with Obelix, which propelled him to the sport's highest levels. In 2009, Darragh and Obelix won the $100,000 Budweiser FEI World Cup™ Qualifier of Syracuse CSI4*-W, followed by a victory in the $100,000 World Cup™ Qualifier CSI2*-W and notable third-place finishes in the $250,000 FTI Grand Prix and FEI World Cup™ Qualifier CSI4*-W in 2010.

Over the following years, Darragh continued to achieve impressive results in prestigious grand prix classes along the East Coast. In September 2012, he made the bold decision to leave North Run Farm and establish Oakland Ventures, LLC. Since its inception, Oakland Stables has emerged as a leading competition barn, known for its high-performance sales horses and elite training programs in Wellington, Florida, and the Netherlands.

Darragh represented Ireland at the 2014 Alltech FEI World Equestrian Games™ in Normandy, where he finished twelfth individually aboard his first championship mount, Imothep. He went on to secure a monumental win as part of the Irish show jumping team, clinching the Aga Khan Trophy and the 2015 Furusiyya FEI Nations Cup™ Jumping CSIO5* at the Dublin Horse Show with Sans Soucis Z.

Darragh's international success continued on the Longines Global Champions Tour, highlighted by two prestigious 5* Grand Prix wins in the summer of 2019: the LGCT Grand Prix of Chantilly and the €500,000 Rolex Grand Prix at Knokke Hippique. He helped secure Olympic qualification for Ireland by jumping double-clear with Balou du Reventon to win team gold in the 2019 Longines FEI Jumping Nations Cup™ Final at CSIO Barcelona. Darragh concluded 2019 with impressive runner-up finishes in the Longines FEI Jumping World Cup™ Verona CSI5*-W and the IJRC Rolex Top 10 Final, along with a second-place finish in the €1.25 Million Longines Global Champions Tour Super Grand Prix Final.

 In 2021, Darragh was nominated by the Olympic committee to represent Team Ireland in Tokyo, competing with Heathman Farm’s VDL Cartello. His successful partnership with Cartello continued as they achieved a coveted double-clear in the 2021 Longines FEI Jumping Nations Cup™ Final at CSIO Barcelona, securing a second-place finish for Team Ireland. Other highlights from 2021 include winning the LGCT Grand Prix of Monaco with Idalville d’Esprit and a fourth-place finish in the Rolex Grand Prix at Geneva with VDL Cartello.

The 2023 season featured a successful campaign at the Winter Equestrian Festival, where Darragh collected multiple FEI wins aboard Vlock Show Stables’ Volany Du Boisdeville and Chic Chic, including a victory in the $140k Grand Prix CSI3* with Volany and another Grand Prix win with Vancouver Dreams in the $226k GP CSI4*. He capped the season by claiming the leading title in the 2023 Captive One 1.50m Series.

In 2024, Darragh has enjoyed an incredibly successful year, highlighted by a win in the $385,000 Fidelity Investments® CSI5* Grand Prix at the Winter Equestrian Festival aboard Vlock Show Stables’ Amsterdam 27. His success continued with a win in the Longines League of Nations with Team Ireland. Throughout the year, Darragh secured victories at prestigious events including Old Salem, the Devon Horse Show, Upperville & Colt Horse Show, Falsterbo Horse Show, Dinard, Deauville, and the Dublin Horse Show. A standout moment was being selected as the traveling reserve for Team Ireland at the Olympic Games in Paris, marking his second Olympics with VDL Cartello, along with a second-place finish in the Rolex Grand Prix of Spruce Meadows during the Spruce Meadows Masters.