This article offers a global perspective on the intertwined histories of English and Dutch overseas enterprises in the early seventeenth century. The English and the Dutch were close allies in Europe when they embarked on commercial and colonial ventures. This history of alliance provided crucial military training for Englishmen who served in English colonies in Virginia, New England, and the Caribbean. The English and the Dutch were also rivals, especially in the commercial competition for spices in the East Indies. Competition and cooperation in Japan and the Spice Islands culminated in the “massacre” at Amboyna in 1623. This history of enmity and amity shaped later English and Dutch interactions in North and South America (including New England and New Netherland), affected European diplomacy, and helped spark three Anglo-Dutch wars.