[7] In 1899 he was elected Medical Officer for the Rathdown Workhouse Infirmary (subsequently redesignated as St Columcille's Hospital) at Loughlinstown, and he combined this appointment with general practice for 42 years.

[10] Almost immediately after joining the club he won the first prize and challenge cup at its annual tournament,[11] and in May the same year he played his way to the semi-final of the Irish Championship where he met Herbert Lawford, the reigning Wimbledon singles champion.

It took five sets for Lawford to prevail over his nineteen-year-old opponent whose good style and easy, cool play attracted considerable notice.

[26] Recovering from typhoid, he was "totally unfit for hard match play" at the 1892 Irish Championship: he was defeated in the semi-finals of the singles competition and he and Stoker lost their doubles title.

[27] A month later he prevailed over Harry Barlow to win the English Northern Championship for the third time,[28] but in the Wimbledon singles final he was beaten convincingly by Baddeley[29] and, paired with Harold Mahony, lost the "all comers" phase of the doubles competition to Lewis and Barlow (who defeated the Baddeley brothers in the Challenge final).

"[40] In 1895 Pim won the singles and (with Stoker) doubles competitions at the Irish championships for the third consecutive year,[41] but afterwards, rather than compete at Wimbledon, he travelled to the United States with Harold Mahony to play against four Americans in an international tournament at Boston.

Pim was meanwhile concentrating on his medical studies and, on passing the final part of his examinations, was admitted a Fellow of the Royal College of Surgeons in Ireland in November that year.

[50] He lost his matches against Malcolm Whitman and William Larned,[51] but stayed in America to compete in the men's singles at the 1902 US National Championships, where he reached the fourth round, falling victim to Leo Ware.

Interviewed in 1898, Wilberforce Eaves (who had faced all the leading players of the decade) named Pim as the best opponent against whom he had played, considering that "His game, when at its best, has probably never been equalled.

[53] Ernest Meers judged that Pim "seemed to possess more actual genius or natural ability for lawn tennis than anyone I ever met",[54] while Arthur Wallis Myers spoke of his "effortless brilliancy and marvellous versatility".

[55] Mahony prefaced a detailed commentary on Pim's style and strengths with the observation that "His game was of the very severe type yet executed with such ease and nonchalance as to give the impression that he was taking no interest whatever in the proceedings".