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The article discusses the complexity of diplomatic and cultural exchange, assimilation, competition, and cooperation that characterized the alliance between England and Spain in the sixteenth century. It also examines the shared cultural heritage of both countries, their trade agreements, and dynastic marriages that had linked them closely by blood. Moreover, a special attention is given to Philip II's entry into London in 1554 as the new English king, a pivotal moment in the rivalry between the two countries. The general dynamics of the international diplomatic relations between the two are also discussed, demonstrating the balance between honesty and deception, admiration and jealousy, and cooperation and rivalry.