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Sailor · 2002–2026

Robert O'Leary

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Events
38

232 races · 53 race wins

Win rate
29%

29% win rate · 11 of 38

Podium rate
45%

17 top-three finishes

Typically beats
82%

of boats faced (range 81%–84%, 2,364 boats)

Best class ranking
#24

Crew in Star · rating 336

Longest win streak
4

race wins in a row

Most successful partnership
Peter O'Leary

1 wins · 3 podiums in 5 events together · 20% win rate

Biggest lift
Peter O'Leary

+17 points of fleet beaten when sailing together

Longest-running crew
Peter O'Leary

Feb 2018 – Mar 2020 · 5 events

Nemesis
Eivind Melleby

6–18 head to head in 24 races

Rival
Chuck McCarthy

33–28 in 61 races

Best day
1 Jan 2021

2-1-4-1-4-DNF-4-3-2-1-1-4-3-1-DNF-2 · MBSC week 3

Signature result
1st of 47

2017-2018 Miami Star Winter Series - Walker Cup / Midwinters · Star · 8 Feb 2018

Partnerships · 23 sailors

Most successful partnership: Peter O'Leary — 1 wins · 3 podiums in 5 events together · 20% win rate
  • Peter O'Leary · Archie, Dafne, DAFNE · Star 5events 1 wins together · 3 podiums · 20% win rate · 3 of 34 races won Beat 94% of the fleet together(+17 vs. without) · best 1st · Feb 2018 – Mar 2020
  • Sally O'Flynn · Antix · IC37, J/70 2events 0 wins together · 0 podiums · 2 events · 0 of 15 races won Beat 28% of the fleet together · best 18th · Mar 2025 – Jul 2025
  • Anthony O Leary · Antix · IC37 1events 0 wins together · 0 podiums · 1 events · 0 of 8 races won Beat 32% of the fleet together · best 18th · Jul 2025 – Jul 2025
  • David Kelly · 2Farr · Handicap 1events 0 wins together · 0 podiums · 1 events · 3 of 7 races won Beat 86% of the fleet together · best 5th · Aug 2024 – Aug 2024
  • Riaghan Boardman · 2Farr · Handicap 1events 0 wins together · 0 podiums · 1 events · 3 of 7 races won Beat 86% of the fleet together · best 5th · Aug 2024 – Aug 2024
  • Pat Kelly · 2Farr · Handicap 1events 0 wins together · 0 podiums · 1 events · 3 of 7 races won Beat 86% of the fleet together · best 5th · Aug 2024 – Aug 2024
  • Patrick Boardman · 2Farr · Handicap 1events 0 wins together · 0 podiums · 1 events · 3 of 7 races won Beat 86% of the fleet together · best 5th · Aug 2024 – Aug 2024
  • Marty O'Leary · Antix · IC37 1events 0 wins together · 0 podiums · 1 events · 0 of 8 races won Beat 32% of the fleet together · best 18th · Jul 2025 – Jul 2025
  • Derek Moynan · Antix · IC37 1events 0 wins together · 0 podiums · 1 events · 0 of 8 races won Beat 32% of the fleet together · best 18th · Jul 2025 – Jul 2025
  • Nicholas O'Leary · Brotherly Love · Star 1events 0 wins together · 0 podiums · 1 events · 0 of 6 races won Beat 83% of the fleet together · best 12th · Mar 2019 – Mar 2019

Lift shows how much better this sailor finishes with that partner aboard.

Rating history

0268536200320072011201520192023Helm rating, full-size sailingCrew rating, full-size sailing

— Helm rating, full-size sailing · - - Crew rating, full-size sailing

Event history · 38

DateEventBoatClassRoleFinish
1 Jan 20261720 European Championships 2026SwiftBoneHandicapSkipper5th / 17
1 Jan 2026BSC Baltimore Cup 2026SwiftieHandicapSkipper2nd / 15
1 Jan 2026Doyle Sails 1720 Southerns 2026SwiftieHandicapSkipper1st / 20
1 Jan 2026Rope Doc 1720 National ChampionshipsSwiftieHandicapSkipper2nd / 19
1 Jan 2026Rope Doc 1720 National ChampionshipsSwiftieHandicapSkipper1st / 19
18 Jul 20252025 IC37 National ChampionshipAntixIC37Helm18th / 26
20 Apr 2025RORC Easter Challenge2 FARRIRC handicapSkipper29th / 252
20 Apr 2025RORC Easter Challenge2 FARRIRC handicapSkipper9th / 252
19 Apr 2025RORC Easter Challenge2 FARRIRC handicapSkipper37th / 252
19 Apr 2025RORC Easter Challenge2 FARRIRC handicapSkipper21st / 252
18 Apr 2025RORC Easter Challenge2 FARRIRC handicapSkipper25th / 252
18 Apr 2025RORC Easter Challenge2 FARRIRC handicapSkipper146th / 252
3 Mar 20252025 Bacardi Cup Invitational RegattaAntixJ/70Other38th / 50
5 Aug 2024Half Ton Classics Cup2FarrHandicapCrew5th / 30
1 Jan 20231720 National Championships 2023Dutch CourageHandicapSkipper7th / 27
1 Jan 2023Baltimore CupDutch GoldHandicapSkipper2nd / 16
1 Jan 20211720 July League 2021Dutch GoldHandicapSkipper6th / 9
1 Jan 20211720 Nationals 20212020HandicapCrew1st / 20
1 Jan 2021Audi Waterford 1720 Europeans 2021Dutch GoldHandicapSkipper5th / 27
1 Jan 2021MBSC week 1rob2727HandicapSkipper1st / 16
1 Jan 2021MBSC week 2rob2727HandicapSkipper1st / 16
1 Jan 2021MBSC week 3rob2727HandicapSkipper1st / 15
8 Aug 20201720 August League 2020Dutch GoldHandicapSkipper9th / 10
5 May 2020MBSC VR League May 2020Rob2727HandicapSkipper17th / 18
2 Mar 20202020 Bacardi Cup Invitational RegattaArchieStarFoil Trimmer6th / 66

Helm rating, Full-size sailing: 478, #3,479.Crew rating, Full-size sailing: 468, #2,393. Compiled from public results; not an official ranking.