[9] Littledale, promoted on 1 February 1940 to major,[10] served in World War II where he took part in the defence of Calais, as a Transport Officer with the 30th Infantry Brigade.

[4] With other captured officers he was marched across northern France for about 10 days then taken by train from near Luxembourg to Trier, Mainz and onward to Oflag VII-C Laufen in mid June 1940.

In May 1941, with two other British officers; Lieutenant Mike Sinclair and Gris Davies-Scourfield, he escaped by hiding in a modified handcart carrying rubbish to a pit outside the camp.

[13] Littledale left Switzerland on 25 January 1943, and with Flight Lieutenant Hedley Fowler, who had escaped earlier from Colditz, travelled across unoccupied France.

[16] He was killed in action on 1 September 1944, commanding the 2nd Battalion of the King's Royal Rifle Corps and is buried at Airaines Cemetery in France.