As the son of two trainers, Darragh began competing in the sport of show jumping at the age of 10 in his homeland of Offaly, Ireland. Kenny’s career quickly flourished as he competed in his first grand prix at the young age of 14 and was invited to compete at the Dublin Horse Show, where he won a training bursary to work with a top American coach in 2007 at the age of 19.

Shortly after, Kenny began working with North Run Farm under the tutelage of Missy Clark and John Brennan. With the help of Clark, Kenny acquired the ride on Obelix, a horse that guided him to the top level of the sport. In 2009, the pair captured the $100,000 Budweiser FEI World Cup™ Qualifier of Syracuse CSI4*-W, followed by another victory in the $100,000 World Cup™ Qualifier CSI2*-W as well as third-place finishes in the $250,000 FTI Grand Prix and FEI World Cup™ Qualifier CSI4*-W in 2010.

Over the next few years, Kenny continued his steady and impressive climb with top placings in prestigious grand prix classes up and down the East Coast. In September 2012, Kenny made the difficult decision to leave North Run Farm and form his own Oakland Ventures, LLC. 

Since its inception, Oakland Stables has become one of the most successful competition barns, offering high-performance sales horses and an elite training program with bases in Wellington, Florida and Meijel, Netherlands.

Kenny represented Ireland in the 2014 Alltech FEI World Equestrian Games™ in Normandy, France, where he placed twelfth individually aboard his first championship mount, Imothep. From there, Kenny captured a monumental victory as a member of the Irish show jumping team, winning the Aga Khan Trophy and the 2015 Furusiyya FEI Nations Cup™ Jumping CSIO5* with Sans Soucis Z on home turf at the Dublin Horse Show.

In recent years, Kenny has continued to produce exceptional results internationally and on the Longines Global Champions Tour. He boasts an impressive resume of countless accolades with two prestigious 5* Grand Orix wins in the summer of 2019, which include the LGCT Grand Prix of Chantilly and the €500,000 Rolex Grand Prix in Knokke Hippique. 

Kenny helped to earn Olympic qualification for Ireland after jumping double-clear with Balou du Reventon to win team gold in the 2019 Longines FEI Jumping Nations Cup™ Final at CSIO Barcelona. He concluded a successful 2019 with impressive runner-up positions in the Longines FEI Jumping World Cup™ Verona CSI5*-W and the IJRC Rolex Top 10 Final, while also finishing second in the €1.25 Million Longines Global Champions Tour Super Grand Prix Final with Balou du Reventon.

 In 2021, Kenny was nominated by the Olympic committee to represent Team Ireland in Tokyo, where he competed with Heathman Farm’s VDL Cartello. Continuing with great success aboard Cartello, Darragh rode to a coveted double-clear in the 2021 Longines FEI Jumping Nations Cup™ Final at CSIO Barcelona, helping to secure Team Ireland’s second place finish on the podium. Other successes in 2021 include a win in the LGCT Grand Prix of Monaco with Idalville d’Esprit and closing the year with a 4th place finish in the Rolex Grand at Geneva with VDL Cartello.

Throughout 2022, the team at Oakland Stables has welcomed a number of new rides to the team, making Kenny’s team an exciting mix of young horses and experience upper level partners. Competition at the Winter Equestrian Festival started the year on a high note, as Kenny collected the win in the $37,000 Douglass Elliman 1.45m CSI5* with Vlock Show Stables’s Chic Chic, the $75,000 1.50m Classic CSI4* with Vlock Show Stables’ Volnay Du Boisdeville, and the win in the $216,000 Grand Prix CSI4* with Volnay. The year has continued to bring a number of wins and placings throughout the Global Champions Tour in Mexico, Madrid, Stockholm, Paris, and Monaco in addition to a 9th place finish in the Rolex Grand Prix of Aachen with VDL Cartello.

Darragh currently sits within the top-20 on the Longines FEI World Rankings with an impressive string of horses that have helped him curate top results throughout 2023. He began the year competing at the Winter Equestrian Festival (WEF), where he collected multiple FEI wins aboard Vlock Show Stables’ Volany Du Boisdeville and Chic Chic, including a win in the $140k Grand Prix CSI3* with Volany and another Grand Prix win with Vancouver Dreams in the $226k GP CSI4*. Darragh ended the season on a high note and walked away with the leading title in the 2023 Captive One 1.50m Series. Following WEF, Darragh began a successful summer tour at Spruce Meadows, which was highlighted by a 6th place finish in the coveted Queen Elizabeth Cup aboard Heathman Farm’s Hamrah Van Het Exelhof Z. Continuing through the summer, Darragh competed heavily on the Major League Show Jumping Tour throughout North American, where his team collected overall champion honors for the season after countless podium finishes.