Dorsetshire was one of the ships which engaged the fleeing German battleship Bismarck in late May 1941 in the North Atlantic. On 27 May Dorsetshire was ordered to torpedo the Bismarck, which had by that point been cripped by repeated aircraft and naval attacks. Bismarck sank rapidly, and Dorsetshire was able to recover only 115 of her crew from the sea, before being forced to evade a suspected U-boat. Her captain at the time was Augustus Agar.
Dorsetshire also chanced upon the German supply ship Python on December 1, 1941, whilst she was refueling U-boats in the South Atlantic. The submarines dived, and one of them fired torpedoes at Dorsetshire which missed. The crew of Python scuttled their ship.
Dorsetshire and another cruiser, HMS Cornwall, were sunk by Japanese dive bombers in the in the Indian Ocean (west of Ceylon) on April 5, 1942. Most of the crew were lost. Capt. Agar was among the survivors.