The first Head of the Dog was run in November 1987 and consisted of the Bartlett Challenge Pairs competition. There were 3 entries including the rarely sighted mixed pair.
Nineteen years later the regatta has perpetual silver trophies for Men's 1x, Women's 1x, K1, the Spirit of the Dog award, and the highly coveted Best of Breed for the best costume worn during the race. Notable winners have been the French maids Tiffany and Stephanie, Big Bo Peep and her dog, The Weber Masters, and Schlenker and Devine Plumbing.