The Macartney Embassy has long been known as the first official Anglo-Chinese encounter, whose failure has been extensively studied. This article makes use of five little known historical documents to re-evaluate these earliest encounters, including the first English attempt at trading with China in 1553; the first letter addressed to the King of China in 1583; the 1787 letter intended to be carried by the first ambassador to China; the 1793 Qing Court Memorial with Qianlong Emperor’s comments; and the 1795 reply from King George Ⅲ to the Qianlong Emperor’s letter brought back by Macartney. These under-researched documents not only contextualise the Anglo-Chinese encounters in moving back the timeline to the mid-sixteenth century, but also reveal the underpinning incompatible world views as the much more fundamental reasons behind the failure of the Macartney Embassy, which are still highly relevant and illuminating for understanding today’s relationship between China and the West.