[2] Under his supervision as secretary of the All England Club from 1907 to 1925, the Wimbledon Championships moved to its current site at Church Road.

In 1879, he was promoted to midshipman and was assigned to HMS Bacchante which toured the colonies of the British Empire around the world from 1880 to 1882.

[9] Blanche was the daughter of a wealthy tailoring business proprietor from London, and a successful tennis player.

Only five days after the wedding, the newly married couple competed at the Middlesex Championships at Chiswick Park, and won the mixed doubles title.

He reached the 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.

[10] In 1897, he won the first staging of the International German Championships at Hamburg, beating George Ball-Greene in five sets in the final.

At the 1901 Wimbledon singles, he beat Laurence Doherty in the third round before losing in the quarter-finals to Arthur Gore.

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.

[12] In 1908, he competed at the London Olympic Games and won the gold medal in doubles alongside Reginald Doherty.

Later that year, he participated in a trip of English cricketers to North America led by Lord Hawke in winter 1891/92.

[14] Upon his return, Hillyard occasionally played cricket for another two years, making a total of 49 first-class matches in his career.

[16] The Hillyards frequently hosted popular house parties with tennis champions such as Norman Brookes, Harold Mahony, Anthony Wilding, May Sutton, Violet Pinckney and Dora Boothby as guests.

[17] With the success of the Wimbledon tournament, the necessity to move the ground from his initial location at Worple Road to a larger site became obvious.

This had been discussed as early as Hillyard became secretary in 1907, but searching for a better suitable site took time, and the outbreak of World War I further postponed the issue.

As the secretary, Hillyard was probably heavily involved in the search for, and selection of the new site at Church Road, and worked together with architect Stanley Peach.

Hillyard had been on a tennis tour in South Africa the winter before where he had played on courts made of crushed up ant heaps.

The first court was laid out at Hillyard's home at Thorpe Satchville, and was called En-tout-cas (literally "in all cases") upon the idea of a guest, a French lady.

Their new house was of similar size, and Hillyard again constructed two tennis courts,[24] but began to focus on playing golf.