doubles final twice at Wimbledon with Ernest Lewis in 1889 and 1890, but lost to the Renshaw brothers and Joshua Pim and Frank Stoker, respectively. Alongside Harry Scrivener, he won the doubles title at the British Covered Court Championships in 1890 and 1891. The following years, his focus shifted again to cricket, playing for Leicestershire, until 1896 when he won the singles, doubles, singles handicap and mixed doubles (with his wife) at Monte Carlo. In 1897, he won the first staging of the International German Championships at Hamburg, beating George Ball-Greene in five sets in the final. He repeated his success at Hamburg in 1900. At Wimbledon singles, early losses enabled him to win the All England Plate in 1898, and reach the final in 1899. At the 1901 Wimbledon singles, he beat Laurence Doherty in the third round before losing in the quarter-finals to Arthur Gore. In 1905, at 41 years of age, Hillyard lost the final at the Bad Homburg tournament against Anthony Wilding. He entered the Wimbledon Championships 1906, conceding a walkover to Arthur Gore. Being assigned secretary of the All England Club in 1907, he never entered the Championships again. However, he did continue to play minor tournaments such as at Eastbourne, Yorkshire and Leicester until 1914. After the Great War, at 55 years of age, he competed at his home tournament at Leicester and even won the mixed doubles alongside Gladys Lamplough. In 1908, he competed at the London Olympic Games and won the gold medal in doubles alongside Reginald Doherty. However, although being great fan of the Olympics in general, he was less enthusiastic about the idea of tennis being a part of it. In his book Forty Years of First Class Lawn Tennis, published in 1924, he wrote: "As for lawn tennis in conjunction with the Olympic Games, the whole thing is a inconguous farce. You could as well have Olympic cricket or Olympic golf. It is difficult to believe that players or public can treat the matter seriously or care two straws about it. Why it is wanted, or tolerated, when we already have the Davis Cup, is beyond my comprehension." Cricket During his time at the Navy, Hillyard played a lot of different sports, but concentrated on cricket, and even was captain of the cricket team for two years. Afterwards, he made his first appearance for Middlesex against the Marylebone Cricket