In 1881, he was a surgeon and medical practitioner. In 1888 he was a divisional surgeon of police at Wimbledon.

In the 1891 and 1896 directories, his father, also called Other Windsor Berry, was listed as living at 7, Glebe Villas, Whitford Lane. His father was still at this address when he died in 1901, as shown in his will. His father left him and his brother £1,352 13s. When Other Windsor Berry died in 1908, he left £5,652 17s. 6d. (£700,000 in 2020 values).

He gave evidence in the murder trial of George Henry Lamson at the Old Bailey, 27th February 1882, who was accused of murdering Percy Malcolm John, a pupil at Blenheim House School at Wimbledon. He said:

I am a surgeon and registered medical practitioner, practising at Wimbledon

— I knew the deceased Percy Malcolm John, and had known him about a year and a half; I had frequently seen him before the 3rd of December — I had attended him for one slight illness in March, 1881, while he was at the school—it was a little skin eruption—in June, 1881, I vaccinated him—those were the only occasions—with the exception of the paralysis of his lower limbs his health I believe was generally good

Source : Old Bailey Proceedings Online (www.oldbaileyonline.org, version 8.0, 25 November 2020), February 1882, trial of GEORGE HENRY LAMSON (29) (t18820227-367).

In 1888, he gave evidence in a trial at the Old Bailey on 2nd July 1888, against Charles Savage, 21, and Elizabeth Thatcher, 18, for robbery with violence on George Northcroft (Policeman V 265), and stealing 1s. 5d. and a silver watch and chain.

he said:

I am divisional surgeon of police at Wimbledon.

— I saw the prosecutor at the station about 1 on this morning — his face was bruised and swollen; the left eye actually closed from a blow — there was a wound from a quarter to half an inch long over his left eye, and abrasions on the cheek and upper lip from scratches—the throat was swollen, with marks of pressure on it — he is still off duty, and has been under my care since that time.

Source : Old Bailey Proceedings Online (www.oldbaileyonline.org, version 8.0, 25 November 2020), July 1888, trial of CHARLES SAVAGE(21) ELIZABETH THATCHER(18) (t18880702-707).

Extracts from the Old Bailey Proceedings project, courtesy of Tim Hitchcock, Robert Shoemaker, Clive Emsley, Sharon Howard and Jamie McLaughlin, et al., The Old Bailey Proceedings Online, 1674-1913 (www.oldbaileyonline.org, version 7.0, 24 March 2012).