His father was the tenth of the eleven children of Brigadier John Pennycuick (1789–1849), who was killed in the Battle of Chillianwala in the Second Anglo-Sikh War.
[7] He was appointed as a High Court judge in 1960,[8] in the Chancery Division, and received the customary knighthood.
Pennycuick became the first modern Vice-Chancellor in July 1970 when the office was revived to replace the title of "Senior Judge" for the head of the Chancery Division.
[11] In major tournaments between 1925 and 1931, he competed at the Wimbledon Championships six times in the men's singles events.
[12] He advanced to the third round in 1925 where he lost to the Indian player Jagat Mohan Lal,[13] and 1926 where he was beaten by Czech international Jan Koželuh.