[1] In 1899, he played regularly as a lower-order batsman and bowler and in the match against the MCC he took five second-innings wickets for 47 runs, the best bowling performance of his first-class cricket career.
[4] There was then a hiatus in Penn's university and cricket career, as he joined the 3rd (Militia) battalion of the Royal Scots as a lieutenant on 30 August 1899.
The battalion was embodied in December 1899 to serve in the Second Boer War, and in early March 1900 left Queenstown on the SS Oriental for South Africa.
[5][2] He returned to both Cambridge and cricket for the 1902 season, when he had less success as a bowler but more as a batsman, scoring 51 not out in the match against Ireland, his only half-century.
[1] On the outbreak of the First World War, Penn joined the Norfolk Yeomanry; he transferred to the 4th Battalion of the Grenadier Guards in April 1915 and was promoted to the rank of captain in September that year, a month before he was killed in the fighting of the Battle of Loos.