King Philip II was married to four different women, Anna of Austria being the fourth. None of Philip’s three previous wives provided him with a male heir to the throne. So, Philip arranged a marriage with his 21 year old niece Anna. Anna was born to Philip’s sister Maria and the Holy Roman Emperor Maximillian II. Through the course of Philip and Anna’s marriage, they were able to have five children, four of which were male. Of the four, only Philip III survived to adulthood.

The obverse text PHILIPPVS HISPANIAR • ET • NOVI ORBIS OCCIDVI REX translates to Philip, King of Spain and of the New Western World.

The obverse shows a bearded bust of King Philip II facing the left side of the medal. He is wearing his royal armor with an intense look on his face. Surrounding the bust is the inscription above. On the outer edge of the medal is a dotted border.

The reverse text • ANNA • AVSTRIACA • PHILYPPI • CATHOL • ÆT.Z1 translates to Anna of Austria, Philip the Catholic, Age 21 (referring to Anna’s age).

The reverse shows a young bust of Anna of Austria facing the right side of the medal. She is wearing a high ruff and her hair is in a decorative net that was typical of the period. Surrounding the bust is the inscription above. On the outer edge of the medal is a dotted border. The inscription with Anna’s age is located on the lower portion of her bust, as shown below.