Proposed by Hans Nadorp during the Annual General Meeting of 1999 in Torbole, the Classic Cup is sailed at the same time as the Gold Cup by the “Classics". The idea was to promote both the classic yachts and the Gold Cup by giving the first a cup of their own and to the second a larger fleet. Both competitions have some similarities in their rules. The Classic Cup is now a fleet racing series.

The first edition of the Classic Cup was disputed in Medemblik a few days before the World Championship 2000 and the first winner was the Dutch boat of Piet van Opzeeland - Topaze - racing for the Netherlands. In recent years "Carabella" has been dominating the scene, with "Apriori" constantly showing comparable performance.
The Past Winners
2011 Helsinki, ITA-73 Carabella (Chance 70), Alfredo Delli
2010 Torbole, ITA-73 Carabella (Chance 70), Alfredo Delli
2009 Hanko, ITA-73 Carabella (Chance 70), Alfredo Delli
2008 Nassau, ITA-73 Carabella (Chance 70), Alfredo Delli
2007 San Remo, ITA-73 Carabella (Chance 70), Alfredo Delli
2006 Medemblik, ITA-73 Carabella (Chance 70), Alfredo Delli
2005 Sydney, ITA-73 Carabella (Chance 70), Alfredo Delli
2004 Hanko, FIN-26 Chaje 3 (Luders 1964), Matti, Uula and Matias Muoniovaara
2003 Thun, NED 11 Topaze, Piet van Opzeeland
2002 Helsinki, FIN-26 Chaje 3, Matti, Uula & Matias Muoniovaara
2001 Flensburg, NED 13 Tripel, Sander Van der Post
2000 Medemblik, NED 12 Topaze, Piet van Opzeeland