Chicago - Mackinac Cup Race to Mackinac Division Trophy Elapsed Year Boat Owner Club Type of Yacht Time Division 1898 Vanenna William R. Crawford Chicago YC Joseph Myers 64' Sloop 52:17:50 Fleet 1904 Vencedor Fred A. Price Columbia YC 47' Sloop 37:46:00 Fleet 1905 Mistral Dwight Lawrence Chicago YC 48' Schooner 94:10:00 Fleet 1906 Vanadis George S. & Lloyd R. Steere Chicago YC Auxiliary Yawl 62:07:46 Fleet 1907 Vencedor George Tramel Chicago YC 47' Sloop 43:29:00 Fleet 1908 Valmore William Hale Thompson Chicago YC 81' Schooner 52:21:50 Fleet 1909 Valmore William Hale Thompson Chicago YC 81' Schooner 42:33:33 Fleet 1910 Valmore William Hale Thompson Chicago YC 81' Schooner 31:24:06 Fleet 1911 Mavourneen Edward M. Mills Chicago YC 30' sloop 37:57:00 Fleet 1912-1913 Race to Harbor Springs 1914 Olympian Roy M. Barcal Chicago YC P Class 61:36:00 Fleet 1915 Leda George B. Currier Columbia YC 35' sloop 68:53:22 Fleet 1916 Intrepid Roy M. Barcal & Frank J. Snite Chicago YC P Class 72:16:50 Fleet 1917-1920 Not Sailed 1921 Virginia Carlos Alling Jackson Park YC Q Class 45:37:25 Fleet 1922 Intrepid Donald F. Prather & Vernon E. Farrell Chicago YC P Class 56:35:00 Fleet 1923 Virginia J.A. Hadwiger Chicago YC Q Class 62:37:26 Fleet 1924 Sari Benjamin Carpenter, Jr. Chicago YC R Class 56:54:30 Fleet 1925 Virginia J.A. Hadwiger Chicago YC Q Class 70:48:50 Fleet Donald F. Prather, Louis C. Brosseau, Frank W. 1926 Intrepid Hough, George Woodruff Chicago YC P Class 58:37:35 Fleet 1927 Siren William L. Latimer, Leland L. (Ole) & Al E. Karas Chicago YC Q Class 59:31:58 Racing 1928 Comet Howarth D. Beaumont Chicago YC Yawl 67:58:17 Cruising 1929 Blue Moon Harold T. Simmons Jackson Park YC Schooner 47:18:18 Racing 1930 Cynthia John L. Williamson Chicago YC 34' Alden Yawl 76:41:05 Cruising 1931 Siren Leland L. (Ole) & Al E. Karas Chicago YC Q Class 60:45:04 Racing 1932 Bagheera Robert P. Benedict Chicago YC 55' Schooner 67:43:02 Cruising 1933 Siren Leland L. (Ole) & Al E. Karas Chicago YC Q Class 70:26:48 Racing 1934 Elizabeth Lynn A. Williams Chicago YC 51' Schooner 64:47:32 Cruising 1935 Princess Ed Jedrzykowski & Carl A. Kallgren Jackson Park YC Q Class 57:11:47 Racing Chicago - Mackinac Cup Race to Mackinac Division Trophy Elapsed Year Boat Owner Club Type of Yacht Time Division 1936 Rubaiyat Nathanial Rubinkam Columbia YC Alden 44 68:30:38 Cruising 1937 Revenge Blair Walliser & Ken Griffin Chicago YC 59' Cutter 76:38:49 Racing 1938 Manitou James R. Lowe Chicago YC 62' Yawl 45:05:49 Cruising 1939 Gloriant Anthony M. Hermann Racine YC Q Class 62:47:44 Universal 1940 Bangalore Edward B. Lumbard Chicago YC 43' Cutter 69:53:40 Cruising 1941 Lively Lady Otto Dreher South Shore YC Q Class 50:55:15 Universal 1942 White Cloud Charles E. Sorenson Detroit YC 60' Sloop 38:14:05 Cruising 1943 Gloriant Vitas T. Thomas Racine YC Q Class 53:32:26 Universal 1944 Bangalore Too Edward B. Lumbard & John D. Kinsey Chicago YC 44' Yawl 71:59:39 Cruising 1945 Cara Mia Leland L. (Ole) Karas Chicago YC Q Class 69:00:55 Universal 1946 Blitzen Ernest Grates & Murray Knapp Detroit YC 55' Cutter 57:33:56 Cruising 1947 Cara Mia Leland L. (Ole) Karas Chicago YC Q Class 46:41:46 Universal 1948 Taltohna Edgar B. Tolman, Jr. Chicago YC 45' Ketch 42:24:31 Cruising 1949 Cara Mia Leland L. (Ole) Karas Chicago YC Q Class 57:00:45 Universal 1950 Fleetwood Nicholas J. Geib Chicago YC Custom 39' Ketch 57:12:24 Cruising 1951 Gale Harry G. Nye Jr. Chicago YC Q Class 52:54:26 Universal 1952 Tahuna Peter C. McNulty Milwaukee YC 40' Yawl 48:51:07 Division 1 1953 Fleetwood Nicholas J. Geib Chicago YC Custom 39' Ketch 60:57:57 Division 2 1954 Taltohna Edgar B. Tolman, Jr. Chicago YC 45' Cutter 68:50:12 Division 1 1955 Rangoon David B. Silberman & Albert E. Stern Columbia YC 37' Sloop 88:56:23 Division 2 1956 Copperhead Charles L. Kotovic Milwaukee YC Yawl 48:47:29 Division 1 1957 Meteor III Henry Burkhard Bayview YC 38' Cutter 50:37:11 Division 2 1958 Dyna Clayton Ewing Chicago YC Sparkman & Stephens 58' Design #1177 yawl 64:45:05 Division 1 1959 Feather II William G. Peacock, Jr. Columbia YC 32' Yawl 63:48:03 Division 2 1960 Freebooter Mac & Robert Pohn Columbia YC Burgess Rigg & Morgan 58' Ten Meter cutter 48:19:09 Division 1 1961 Blue Horizon Dick Kaup Chicago YC Rhodes 34' Cutter 61:05:38 Division 2 1962 Flame James E. Doane Chicago YC Kettenberg 40 63:47:51 Division 1 1963 Meteor III Henry Burkhard Bayview YC 38' Cutter 57:03:21 Division 2 1964 X-Barb Dr. David Axelrod Jackson Park YC Owen Cutter 61:46:25 Division 1 1965 Challenge Robert R. Rothchild Chicago Corinthian YC Alberg 30 76:01:32 Division 2 Chicago - Mackinac Cup Race to Mackinac Division Trophy Elapsed Year Boat Owner Club Type of Yacht Time Division 1966 Blitzen William & Thomas Schoendorf South Shore and Chicago YC Sparkman & Stephens 55' Design #221 cutter 57:52:36 Division 1 1967 Flying Buffalo Karl Ness & Maurice DeClercq Bayview YC 34' Sloop 51:58:33 Division 2 1968 Comanche William & Thomas Schoendorf South Shore YC Chris-Craft 42 40:21:27 Division 1 1969 Flying Buffalo Karl Ness & Maurice DeClercq Bayview YC 34' Sloop 72:14:11 Division 2 1970 Dora Lynn A. Williams, Jr. Columbia YC Palmer Johnson 55 36:58:23 Division 1 1971 Endurance Roger H. Derusha Marinette & Menominee YC C&C 43 51:18:41 Division I 1972 Azure Edward Lekan & Robert Haagenson Chicago YC WTN 30 52:57:18 Division IV 1973 Bay Bea Patrick F. Haggerty Sturgeon Bay YC Sparkman & Stephens 49 59:43:14 Division I 1974 No Go VII Ed Siegle & Grant Crowley Chicago Corinthian YC Wylie 39 46:44:51 Division II 1975 Dora IV Lynn A. Williams, Jr. Chicago YC Sparkman Stephens 61 45:03:25 Division I 1976 Tortuga Richard Wharton & Bruce Creger Burnham Park YC Pearson 30 60:32:10 Division IV 1977 Awarded jointly to all section winners 1978 Scaramouche Charles E. Kirsch Chicago YC Frers 48 48:06:17 IOR 1979 Chocolate Chips Ron Lester & Bill Porter Michigan City YC Grahm & Schlageter 34 48:55:04 IOR 1980 Rush R. Kristen Hicks Little Traverse YC Nelson Marek 35 59:35:31 IOR 1981 Thunderbird Richard Mashke & John Erb Columbia YC Custom Cook 35 64:46:58 IOR 1982 Leading Edge Eugene Mondry Bayview YC North American 40 52:19:50 IOR 1983 Thirsty Tiger Albert G. D'Ottavio Chicago YC Orca 43 59:07:20 MHS 1984 Heritage Sea Scouts Sea Scouts Charles Morgan 63' 12 Meter 35:15:41 IOR 1985 Hilaria Robert Stocker Chicago YC Sparkman & Stephens 55 47:24:46 MHS 1986 Eagle Jerome F. O'Neill Chicago YC Farr 33 46:59:44 IOR 1987 Glider John Huff & Richard Stearns Chicago YC Tartan 10 34:30:39 IMS 1988 Jeannine Jack O. Roeser Columbia YC Grahm & Schlageter 35 53:22:24 IOR 1989 Insatiable Fred Krehbiel Chicago YC Nelson Marek 45 67:20:45 IMS 1990 Kodiak Edwin L. Ecclestone Bayview YC Frers 67 31:46:06 IMS 1991 Wizo Willard J. Harman Michigan City YC Ericson 39 49:02:01 IMS 1992 Cynosure Terry Kohler & Peter Reichelsdorfer Sheboygan YC Santa Cruz 70 35:37:23 LMPHRF 1993 Daybreak Robert Chatain, Jr. Chicago YC J33 39:45:09 LMPHRF 1994 Windquest Richard M. DeVos Macatawa Bay YC Reichel Pugh 70 44:29:00 LMPHRF 1995 Flash Gordon 2 Helmut Jahn Chicago YC Farr 43 42:30:15 IMS Chicago - Mackinac Cup Race to Mackinac Division Trophy Elapsed Year Boat Owner Club Type of Yacht Time Division 1996 Bantu Thomas J. Kuber Marinette & Menominee YC Block Island 40 51:09:42 PHRF 1997 Wizo Willard J. Harman Michigan City YC Ericson 39 44:10:04 IMS 1998 Bacchant Jerome E. Sullivan Milwaukee YC 75 Square Meter 39:22:14 PHRF 1999 Pied Piper Richard E. Jennings Burnham Park YC Santa Cruz 70 40:50:18 IMS 2000 Sayonara Larry Ellison Saint Francis YC Farr 80 41:32:34 PHRF 2001 Equation William Alcott Bayview YC Great Lakes 70 37:11:22 One Design 2002 Illusion Robert Brandenburg Chicago YC Mumm 30 34:53:22 Cup 2003 Bantu Thomas J. Kuber Marinette & Menominee YC Block Island 40 52:47:00 Cup 2004 Esmeralda Makotu Uematsu Seabornia YC Transpac 52 51:51:03 Cup 2005 Kutty's Ark George Morrisey & Joe McGinnis Columbia YC Pearson 36 50:48:52 Cup 2006 Eagle Jerome F. & Shawn O'Neill Chicago YC Sydney 38 45:33:47 Cup 2007 Vytis Tomas & Gytis Petkus Columbia YC J105 61:54:20 Cup 2008 Stripes Bill Martin Bayview YC Great Lakes 70 41:46:12 Cup 2009 The Asylum Jon Weglarz Chicago YC J105 61:49:42 Cup 2010 Flying Jenny VI David & Sandra Askew Annapolis YC J122 46:54:21 Cup 2011 Usual Suspect Bryan Sims Bronte Harbour YC C&C 43 44:40:20 Cup Tie Fast Tango Tim Prophit & Peter Wenzler Bayview YC North American 40 47:30:35 Cup 2012 Realt Na Mara Tom & Joe Londrigan Island Bay YC J109 42:17:06 Cup 2013 Providence Jerry & Greg Miarecki Chicago YC Ericson 35 MK II 73:59:52 Cup 2014 To The Moon Robert Berg & Katie Berg New York YC Swan 42 41:07:36 Cup 2015 Odyssey David Bohl Milwaukee YC Tartan 34C 54:20:48 Cup 2016 Natalie J Philip & Sharon O'Neil III Bayview YC Transpac 52 26:15:55 Cup 2017 TOA Bruce Danly & Jim Mitchell Chicago YC J109 54:28:57 Cup 2018 Equation William Alcott & Tom Anderson Bayview YC Santa Cruz 70 37:27:00 Cup 2019 Goat Rodeo Robert Evans Sommerset Pointe YC J109 51:02:04 Cup.