Chesapeake 20s were a sanctioned Chesapeake Bay Yacht Racing Association from 1942 until 1968 at which point they did not have enough members to qualify as a sanctioned fleet.  The fleet was re-instated in 2008.  Below are the High Point winners from 1942 until 1968, and 2008.

Early racing history from archives and interview with John Kramer, former owner of Chesapeake 20 named Stormy 00.