 For a cruise that includes an exceptional feat of navigation and/or seamanship | ||
| 1959 P.H. Green Ann Gail | 1960 R.I. Morrison Vanja IV | 1961 R O’Hanlon Harmony |
| 1962/63 No Award | 1964 J.D. Faulkner Angelique | 1965 J.H. Guinness Sharavogue |
| 1966 PH Greer Helen of Howth | 1967 No award | 1968 PH Greer Helen of Howth |
| 1969 No Award | 1970 JP Jameson Ganiamore | 1971 R Courtney Bandersnatch |
| 1972/73 No Award | 1974 J.P. Bourke Korsar | 1975/78 No Award |
| 1979 J Gore-Grimes Shardana | 1980 J Wolfe Deerhound | 1981/82 No Award |
| 1983 K & . Martin Estrellita | 1984 No Award | |
| From 1985 onwards the Rockabill Trophy was awarded for ‘A Feat of Exceptional Navigation/Seamanship’ | ||
| 1985 J. Gore-Grimes Shardana | 1986 John Olver Moody Blue | 1987 J.B. Law Redwing/Spirit of Shell |
| 1988 No Award | 1989 Colin Chapman Deerhound | 1990 Colin Chapman Deerhound |
| 1991 Wallace Clark Aileach | 1992 Peter Bunting Gulkarna II | 1993 Bernard Corbally L’Exocet |
| 1994 Peter Hogan Molly B | 1995 Brian Smullen Zaberdast | 1996 Tom Foote White Heather |
| 1997 Paddy Barry & Jarlath Cunnane Tom Cream | 1998 No award | 1999 Donal Lynch Laroha |
| 2000 Susan & Peter Gray Waxwing | 2001 No award | 2002 John Gore-Grimes Arctic Fern |
| 2003 Ed Wheeler Witchcraft of Howth | 2004 Jarlath Cunnane Northabout | 2005 Brian Black Caelan of Strangford |
| 2006 John Clementson Faustina II | 2007 No award | 2008 Paul Bryans Odysseus |
| 2009 Wallace Clark Agivey | 2010 Tom Foote Picnic | 2011 Norman Kean Xanadu |
| .2012 Brian Black Seafra | 2013 Sam Davis Suvretta | 2014 Norman Kean Arcin |
| 2015 Paul Cooper Drumbeat | 2016 No award | 2017 Michael Madsen Gabelle |
| 2018 Paul McSorley Viking Belle | 2019 Donal Walsh Lady Belle | 2020 Máire Breathnach Annabel J |
| 2021 No award | 2022 No award | 2023 Paul Conway & Gillie Fletcher Cevantes |