The outbreak of the Second Boer War the same month saw the regiment sent to South Africa, where they took part in the Ladysmith Relief Column.

[1] He was 23 years old serving during the Second Boer War when the following deed took place on 3 March 1901 near Derby, South Africa for which he was awarded the Victoria Cross.

On 3rd March, 1901, Lieutenant Dugdale, who was in command of a small outpost near Derby, having been ordered to retire, his patrol came under a heavy fire at a range of about 250 yards, and a Sergeant, two men, and a horse were hit.

[2]He had a severe attack of enteric fever, and after his recovery served with General John French in the Cape Colony.

[1] Staying with his regiment in South Africa until the war ended in May 1902, he then left for the United Kingdom on the SS Briton two months later.