The 2011 National Hunt Chase, Chicago Grey and Derek O’Connor being led in by John Earls and Padraig King after winning for trainer Gordon Elliott \ Healy Racing

Cheltenham, 2011 Zemsky and Derek O’Connor won the champion hunter chase \ Healy Racing

Ballingarry in 2011, title contenders for the point-to-point champion, Derek O’Connor and runner-up Jamie Codd \ Healy Racing

Loughrea 2011, the late John Thomas McNamara congratulates Derek O’Connor after he rode six winners at the meeting \ Healy Racing

Maralin 2011, Jumping style, Buckers Bridge and Derek O’Connor jump the last to win \ Healy Racing

2014 Cragmore, Derek with wife Carol and baby Jessica after Death Duty was Derek’s landmark 1,000th point to point winner \ Healy Racing

The Unibet Irish Gold Cup win for Derek O’Connor on Edwulf \ Inpho/Morgan Treacy

Cheltenham 2019, Derek O’Connor with the trophy for the Fulke Walwyn Kim Muir Challenge Cup Amateur Riders Handicap Chase won by Any Second Now \ carolinenorris.ie

Its On The Line and Derek O’Connor took the Randox Foxhunters’ Open Hunters’ Chase in 2024 \ Mark Cranham-focusonracing.com

2025 Punchestown, Derek O’Connor with wife Carol and kids Annabell, Jessica and Abbie after Its On The Line won the Event Power Champion Hunters Chase \ Healy Racing

Pointing men, Loughrea 2025, Derek and Nimba win for Pat Doyle and Walter Connors \ Healy Racing

Ballysteen last April, Military Saint and Derek O’Connor win for trainer Pauric O’Connor \ Healy Racing

Galway 2026: Derek O’Connor and wife Carol after Comfort Zone won the Connacht Hotel (Q.R.) Handicap \ Healy Racing

Point-to-point awards 2006. Leo Powell is joined by past champions, John Thomas McNamara and Enda Bolger in presenting Derek O’Connor with his Champion rider’s trophy for the season 2005-2006 \ Healy Racing.