1501 to 1600 'The Armada in Sight, 1588' by John Lucas depicts Sir Francis Drake playing bowls at Plymouth Hoe
- 1500s
In the early part of the century the population of Plymouth stood at around 3,500.
- 1501
Catherine of Aragon arrived at Plymouth from Spain in October, ahead of her marriage to Arthur, Prince of Wales (Henry VIII's elder brother).
- 1568
Bullion aboard Spanish ships at Plymouth, in December, was seized. This was in response to the Spanish capture of English ships and their treasure cargo off Mexico a few months earlier.
- 1572
A grammar school was founded in Catherine Street by Queen Elizabeth I.
- 1577
Francis Drake left Plymouth, in December, aboard the Pelican to sail around the world. The ship was renamed Golden Hind during the voyage. He completed the circumnavigation in 1580, arriving back in Plymouth in September.
- 1579
Plymouth was ravaged by the plague.
- 1581
Sir Francis Drake became the Mayor of Plymouth in September.
- 1581
Plymouth was again visited by the plague.
- 1586
The Old Customs House was built on the Quay.
- 1588
Sir Francis Drake joined his ship at Plymouth before engaging the Spanish Armada.
- 1590
Sir Francis Drake built a conduit to provide a water supply for Plymouth.
- 1591
James Lancaster embarked from Plymouth, in April, on the first English voyage to the East Indies. He returned in May 1594.
- 1595
Sir Francis Drake and Capt Hawkins sailed from Plymouth, in August, to raid Panama Isthmus.
- 1595
Twenty-two chests of Papal bulls, which had been seized from Spanish raiders in Cornwall, were publicly burnt in Plymouth market place.
- 1596
An English fleet sailed from Plymouth Sound to engage and destroy Spanish ships preparing in the port of Cadiz. This prevented another Armada being assembled.