After the completion of his fourth tour of duty in July 1944 Cheshire was awarded the Victoria Cross. The Victoria Cross is usually bestowed for a particularly marked event of bravery. In Cheshire's case, the award was given for his behaviour over the course of his entire operational career. At the investiture ceremony at Buckingham Palace, both Cheshire and warrant officer Norman Jackson were to receive the VC from King George VI on that day. Despite the disparity in rank, Cheshire insisted they approach the King together. Upon reaching the King, Jackson recalled Cheshire offering "This chap stuck his neck out more than I did – he should get his VC first." The King kept to protocol and awarded the Group Captain first, but Jackson noted he would "never forget what Cheshire said."