[1] He was educated first at Clongowes Wood College and later at Liverpool University, and was one of 600 Old Clongovians to enlist in the army during World War One.

[2] On the outbreak of war he enlisted in the 2nd Life Guards in November 1914 undergoing his training in Combermere Barracks at Windsor.

After a short time with the Life Guards he was granted a commission with the 3rd (Reserve) Battalion, Prince of Wales's Leinster Regiment (Royal Canadians).

On 3 September 1916, during the Somme Offensive, whilst engaged in intense combat in the vicinity of the village of Guillemont, Holland was awarded the Victoria Cross for the following action: "During a heavy engagement, Lt. Holland, not content with bombing hostile dug-outs, fearlessly led his troops through our own artillery barrage and cleared a great part of the village in front.

At the outbreak of the Second World War, Holland again commissioned, serving as administrative officer of the 79th (Hertfordshire Yeomanry) Heavy Anti-Aircraft Regiment, Royal Artillery,[7] then re-joined the Indian Army but was invalided out in 1941.