Skelton is the youngest son of gold medal Showjumping Olympian Nick Skelton, and there was a time when he was leaning towards following the path laid by his father, but he was bitten by the racing bug during a spell working for trainer Reg Hollinshead. 

The budding jockey joined Richard Hannon for a year before it dawned on him that he was going to be too heavy to make it as a professional Flat rider. 

That’s when his ambitions turned to jump racing. Although hailing from a mainly showjumping background, Harry’s grandfather David had horses with David Nicholson. His dad Nick also owned horses with ‘The Duke’, including smart two‐mile chaser Certainly Strong. 

Now, Harry Skelton is recognised as one of the most successful jump jockeys in Britain, known for his sharp professionalism, natural balance in the saddle, and long record of major race victories. He achieved the title of Champion Jump Jockey in the 2020 to 2021 season and later added the prestigious David Power Jockeys Cup to his achievements, a landmark moment that reflected his place among the leading riders of his generation. 

Racing is part of the Skelton family identity. His father, Nick Skelton, is a celebrated Olympic show jumping champion, and his brother, Dan Skelton, is a leading trainer with whom Harry has formed one of the strongest partnerships in the sport. Their shared ambition continues to drive the success of the Warwickshire stable. 

Away from the racecourse, he is known for his commitment to fitness and endurance challenges, including long distance cycling events that allow him to stay in peak condition.