Born in India, raised in Montrose, educated at Cheltenham College and Royal Woolwich Military Academy. Henry Waugh Renny-Tailyour was a great all round sportsman.
In May 1870 in the games between the 2 Royal Military Academies, Woolwich and Sandhurst , he won the 1/2 mile race ( in 2 mins 10), and finished 2nd in the mile. The following month Renny-Tailyour scored a century in the cricket match between the Royal Military Academy and the Royal Engineers. In July 1870 he graduated from the Academy and became a Lieutenant in the Royal Engineers.
In 1871 Renny-Tailyour represented Scotland in the 4th match in the unofficial 'England v Scotland' series, played at The Oval on 18th November. Renny -Tailyour scored in a 2-1 defeat.
Further evidence of the Lieutenant's versatility came when on 5th February 1872 at The Oval when he played (as a forward) in the second ever international under Rugby Football rules. A dead leg received in this match kept Renny-Tailyour out of action for the next couple of weeks, meaning he was unable to play in the 5th 'Alcock International'.
On 16th March that year however he was back at The Oval, playing in the first FA Cup Final, in which the Royal Engineers went down 1-0 to The Wanderers.In 1873 Renny-Tailyour became the only man to represent Scotland at both Rugby and Association when he was one of 4 English based players called into service for the 2nd international. The Oval was again the venue, and in the 10th minute, with England 2-0 ahead, Renny-Tailyour scored Scotland's first ever goal in international football. (England won 4-2).
Renny-Tailyour features prominently in match reports of the Royal Engineers' club matches during the early 1870s, a period during which they were a major force in terms of both results and the evolution of style. In 1871-72 they lost just 1 out of 20 games (the FA Cup Final) scoring 73 to 2. In the 4 seasons 1871-72 to 1874-75 the stats were:
Another of those very rare defeats came in the 1874 FA Cup Final, a 2-0 loss against Oxford University.
Renny-Tailyour won the FA Cup with Royal Engineers at the third attempt in 1875. In a replayed final The Sappers beat Old Etonians 3-0, (after a 1-1 draw), with Renny-Tailyour scoring in both matches.
This seems to have marked the end of Renny-Tailyour's football career. He married in the summer of 1875 (his wife was the sister of Royal Engineers teammate and England internationalist Cecil Wingfield-Stratford).
During the 1875-76 season he was being written about in the past tense in football reports ruing the decline in the Royal Engineers team (and partly attributing this decline to the 'loss' of Renny-Tailyour).
In March 1876 he was appointed Aide De Camp to the Lord Lieutenant of Ireland.
One aspect of Renny-Tailyour's sporting life persisted into the 1880s. His first class cricket career extended from 1873 to 1883. He represented MCC and Kent as well as playing in the Gentlemen v Players matches. In 1880 he scored 266 for Royal Engineers against The Civil Service, an uncommonly high score at the time.