First saw service in India (1577) and then Pessoa was sent to Azores to suppress a revolt led by Don Antoio, who had designs on the Portuguese throne. Later he was director of a trading firm in Malacca (1584).
When a Dutch warship attacked Malacca in collusion with a chieftain of Malacca, he fought bravely but was taken prisoner and held for ransom (1606). After his release Pessoa was appointed commander of a fortress in Macao. It was during his tenure that the natives of the city clashed with the crew of a Japanese ship owned by Lord Arima. Many Japanese seamen were killed and survivors appealed to the Shogun through Lord Arima for justice but the Portuguese rejected all pleas.
Later when Pessoa entered Nagasaki as commander of a mercantile fleet, the Shogunate ordered Lord Arima to take proper steps to make the Portuguese pay indemnity. When he realized that the Japanese meant business, Pessoa set sail in haste, but a storm prevented his flight. A sea battle took place and after three days of bitter fighting Pessoa sank his ships and he perished with his men.