This article considers the power of Philip the Bold, duke of Burgundy and count of Flanders, Artois and Burgundy Palatine, and his attempts to use violence against England to strengthen his rule in the Low Countries, and help to secure his nephew's rule in France. In 1385, and again in 1386, he came close to launching a large‐scale invasion of England with the support of Scotland and of Brittany that had the potential to remove English influence from Flanders and even force Richard II to give up claims to the French throne. The invasions have been considered from a French and English perspective, and in adding a Burgundian view the present article pulls together English, French, Flemish and Scots source to offer a full analysis of the motivations for the invasion, showing the significance of the Hundred Year War for the rulers of Flanders. Philip's planned invasion capitalized on weaknesses in England, on growing hawkish parties in Scotland, on unity in France and on his own power in the Low Countries. Although the invasions never left Sluis, the attempt to retake the initiative, and to change the balance of power in Europe, merits further consideration for the ambition of Philip and for the centrality of the Low Countries for fourteenth‐century Europe.