Montague Dawson was born in London 1890. He joined the Royal Navy during WWI and by the 1930s was already being considered as one of the greatest living marine painters. During WWII he was employed as a war artist. His prolific output made it a betting certainty that at least some of his paintings would include the Rock of Gibraltar – or at least parts of it. Here are some that I have been able to find. I am sure I have missed quite a few.
HMS Donovan sailing out of Gibraltar Harbour in WWI
HMS Devonshire and escort destroyer leaving Gibraltar
The sloop HMS Chrysanthemum in dry dock at Gibraltar c1918
The SS War Redcap unloading at the New Mole c1918
British Cruiser off Gibraltar