No, Winston Churchill and Princess Diana are not related. They come from completely separate branches of the British aristocracy.
Winston Churchill was a descendant of the Churchill family, which has a long and distinguished history in British politics and military affairs. His ancestors include John Churchill, 1st Duke of Marlborough, a renowned military leader, and Sarah Churchill, Duchess of Marlborough, a powerful figure in the court of Queen Anne.
Princess Diana, on the other hand, was a member of the Spencer family, another prominent aristocratic family. Her ancestor, John Spencer, 1st Earl Spencer, served as the Lord Lieutenant of Ireland in the 18th century.
While both families have a rich history in British society, they are not connected through any known genealogical links.