Whitfield was awarded the Distinguished Service Order (DSO), "in recognition of gallant and distinguished services in the Middle East", on 19 August. He then led the battalion in many battles in the Italian Campaign, including in the Allied invasion of Italy in September, followed by the capture of Naples, the crossing of the Volturno Line, both in October, and, fighting in front of the Bernhardt Line, part of the Winter Line, the Battle for Monte la Difensa in December. He briefly commanded the 169th (Queens) Infantry Brigade, his battalion's parent formation, in October and November 1943. In January 1944 he took command of the 15th Infantry Brigade, commanding the brigade in the First Battle of Monte Cassino, later taking part in the Battle of Anzio. He briefly served as a Brigadier on the General Staff of V Corps. In July he became the General Officer Commanding (GOC) 56th (London) Infantry Division, rising from battalion to divisional command in the space of six months. He led the division in the attack on the Gothic Line in the latter half of 1944 and the offensive in Italy in April 1945.