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History: This regiment has been in existence since the Boar War. The Duke of Connaught and Strathearn became colonel-in-chief of the regiment in 1906, and the regiment's name was thus changed to the Duke of Connaught and Strathearn's Own Cape Town Highlanders.

During World War I the Cape Town Highlanders first fought against Germany in German South-West Africa, but was subsequently combined with the Transvaal Scottish Regiment to form the 4th South African Infantry (South African Scottish) Battalion, part of the 1st South African Brigade. (The South African Scottish, like various similar units, was formed by the South African government since a clause in the Defense Act of that time prohibited existing units from serving so far outside the country's borders.) After fighting in the Senussi Campaign in North Africa the brigade was shipped to France, where it took part in many battles between 1916 and 1918, including the famous Battle of Delville Wood. During its time on the Western Front, the South African Brigade and its Scottish heritage 4th Battalion, first served a lengthy stint with the British 9th (Scottish) Division, and following the Brigade's decimation in March 1918, was reconstituted and incorporated in September into the 66th (2nd East Lancashire) Division until the end of the war.

At the outbreak of World War II in 1939 the regiment was again mobilised. However, it did not fight in the first campaign of the South African Army in the war, the Abyssinian Campaign of 1940 to 1941. However, in mid-1941, the regiment was briefly sent to Egypt to escort thousands of Italian prisoners of war to internment camps in South Africa; it returned to Egypt in late June of the same year to join the newly arrived South African 1st Infantry Division in the Western Desert.

The Cape Town Highlanders fought in all of the major battles of the Western Desert Campaign, including the Battle of El Alamein. Indeed, the regiment is one of only three in the world (all of them South African) to have not only the usual two Alamein battle honours "Alamein Defence" and "El Alamein" but a third, "Alamein Box", which resulted from a separate action during the initial defence. This action played a significant role in halting Rommels advance on the tired and depleted British Eighth Army.

During the regiment's subsequent deployment to Italy, the regiment was temporarily combined with South Africa's senior Scottish unit, the First City Regiment, to form the First City/Cape Town Highlanders. This combined unit fought from Battle of Monte Cassino to the Alps, culminating in the heroic capture at bayonet-point of the strategic peak of Monte Sole as part of the South African 6th Armoured Division.

In 1947, Queen Elizabeth (later Queen Elizabeth the Queen Mother) was appointed colonel-in-chief,