 for the best circumnavigation with special emphasis on navigational and pilotage content | ||
| 1941 E.J. Odlum | 1951 Brendan Maguire Minx of Malham | |
| From 1954 the Navigation Cup awarded for the best cruise around Ireland | ||
| 1954 Wallace Clark Caru | 1955 Dr. R.N. O’Hanlon Ancora | 1956 R.C. Arnold Maid of York |
| 1957 R.P. Campbell Minx of Malham | 1961 C. O’Ceallaigh Julia | 1963 W. & B. Smyth Wynalda |
| 1964 N. Falkiner Euphanzel | 1965 L. McMullen Rainbow | 1967 C.H. Green Helen |
| 1968 J.D. Beckett Dara | 1969 R.E. Mollard Osina | 1971 M. Tomlinson Pellegrina |
| 1973 J. Gore-Grimes Shardana | 1974 R.P. Campbell Verve | 1975 J.B. Law Sai See |
| 1977 G. Leonard Wishbone | 1978 R.P. Campbell & J.R. Osborne Verve | 1979 J. Guinness Deerhound |
| 1980 P. Gray Korsar | 1981 Ronan Beirne Rila | 1982 W.M. Nixon Turtle |
| 1983 A. Doherty Svegala | 1984 J. Guinness Deerhound | 1985 T. O’Keeffe Orion |
| 1986 Brian Hegarty Freebird | 1987 Wallace Clark Wild Goose | 1988 W.M. Nixon Turtle |
| 1989 Tony Morton Lamorna III | 1990 Bernard Corbally L’Exocet | 1991 Robert Barr Ar Men |
| 1993 G Nairn & MD Whelan Lola | 1994 Donal Walsh Lady Kate | 1995 Cormac McHenry Erquy |
| 1996 Michael McKee Isobel | 1997 No award | 1998 Paddy Barry Saint Patrick |
| 1999 Ed Wheeler Witchcraft | 2000 Harry Byrne Alphida of Howth | 2001 Donal Walsh Lady Kate |
| 2002 Sean McCormack Marie Claire II | 2003 Brendan O’Callaghan Brandon Rose | 2004 Alan Rountree Tallulah |
| 2005 No award | 2006 John Delap Sceolaing | 2007 Brendan Bradley Afar VI |
| 2008 Fergus Quinlan Pylades | 2009 No award | .2010 John Madden Bagheera |
| 2011 Donal Walsh Lady Kate | 2012 Paul Butler Muglins | 2013 Donal Walsh Lady Kate |
| .2014 No award | 2015 No award | 2016 Donal Walsh Lady Belle |
| 2017 Garry Villiers Stuart Winny | 2018 No award | 2019 Norman Kean Coire Uisge |
| 2020 Paddy Barry L’Iroise | 2021 Ed Wheeler Witchcraft of Howth | 2022 Derek & Viv White Ballyclair |
| 2023 No Award | ||