At the 1900 Paris Olympics, W. Chester lost his only game in the singes handicap (class II) in three sets to fellow Briton Moreau, who went on to lose the final to the Frenchman Descombes. Chester and Moreau were just two of three non-Frenchmen in a field of 15 starters. In the April prior to the Paris Games, Chester competed in the French Covered Court Championships. After a first-round bye he was then eliminated 6-3, 7-5 by the Frenchman Paul Aymé who went on to reach the semi-finals. At the 1901 Paris International Championships Chester was eliminated in the first round, 6-1, 6-3 by Jean Schopfer.