| 1485 | August | 22nd: Henry VII ascends to the throne |
| 1486 | January | 18th: Henry VII marries Elizabeth of York |
| | September | Prince Arthur is born |
| 1489 | | Princess Margaret is born |
| 1491 | June | 28th, Prince Henry is born |
| 1492 | | Princess Elizabeth is born (dies 1495 aged 3) |
| 1496 | | Princess Mary is born |
| 1499 | | Prince Edmund is born (dies in infancy); Mary Boleyn is born |
| 1500 | | Elizabeth Denton becomes governess to the Princess Mary |
| 1501 | November | Prince Arthur marries Catherine of Aragon |
| 1502 | April | 2nd: Prince Arthur dies |
| 1503 | February | 11th: Princess Catherine is born(dies after three days); Elizabeth of York dies in childbirth |
| 1505 | | (?) Margaret Shelton is born |
| 1507 | | (?) Anne Boleyn is born |
| 1509 | | Jane Seymour is born |
| | April | 21st: Henry VII dies; Henry VIII ascends to the throne |
| | June | 11th: Marriage to Catherine of Aragon; 29th: Margaret Beaufort dies |
| 1510 | May | Affair between Henry VIII and Anne Hastings |
| 1511 | January | 1st: Prince Henry is born (dies in March) |
| 1512 | | Catherine Parr is born |
| 1513 | | Anne Boleyn joins the Court of Margaret of Austria |
| | September–October | Affair between Henry VIII and Etionette de la Baume |
| 1514 | January | Affair between Henry VIII and Elizabeth Blount begins (lasts to 1519) |
| | | Louis XII of France marries Mary Tudor |
| | September | Affair between Henry VIII and Jane Popincourt begins (lasts to January 1515) |
| 1516 | February | 18th: Mary I is born |
| 1518 | | Last recorded pregnancy of Catherine of Aragon |
| 1519 | June | Henry Fitzroy, son of Henry VIII and Elizabeth Blount is born; Elizabeth Blount marries Gilbert Tailboys |
| 1520 | | Affair between Henry VIII and Mary Boleyn begins; Katherine d’Eresby is born |
| | February | 4th: Mary Boleyn marries William Carey |
| 1521 | | Anne Boleyn returns to England from France; Anne Bassett is born |
| 1522 | | (?) Catherine Howard is born |
| 1523 | | Anne Boleyn is courted by Henry Percy, heir to the Earl of Northumberland |
| 1524 | | Mary Boleyn gives birth to either Catherine or Henry Carey |
| 1525 | | Henry Fitzroy is created Duke of Richmond and Somerset and Earl of Nottingham; Affair between Henry VIII and Mary Boleyn ends |
| 1526 | | March Mary Boleyn gives birth to either Catherine or Henry Carey; Affair between King Henry and Anne Boleyn begins |
| 1527 | | Mary Perrot gives birth to John Perrot. |
| | July | First mention of Henry VIII’s divorce |
| 1528 | | William Carey dies |
| 1529 | | Catherine Parr marries Edward Borough |
| 1530 | | (?) Thomas Stukeley is born |
| | November | Cardinal Thomas Wolsey dies |
| 1532 | | Elizabeth Blount marries Edward Fiennes Clinton |
| | September | 1st: Anne Boleyn is created Marquess of Pembroke |
| 1533 | | Catherine Parr marries John Neville, Baron Latimer |
| | January | Anne Boleyn and Henry VIII marry |
| | April/May | Henry VIII divorces Catherine of Aragon |
| | September | 7th: Elizabeth I is born |
| 1534 | | Henry Fitzroy marries Mary Howard; Mary Boleyn marries Sir William Stafford |
| | September | 7th: Katherine d’Eresby marries Charles Brandon, Duke of Suffolk; (?) Affair between Henry VIII and Joanna Dingley |
| 1535 | | (?) Affair between Henry VIII and Margaret Shelton |
| | June | 23rd: Etheldreda Malte is born (?) |
| 1536 | January | 7th: Catherine of Aragon dies |
| | May | 19th: Anne Boleyn is executed; 30th, Henry VIII marries Jane Seymour |
| | July | 22nd: Henry Fitzroy, Duke of Richmond, dies |
| 1537 | October | Jane Grey, briefly Queen Jane I, is born |
| | September | Anne Bassett becomes a lady-in-waiting to Queen Jane |
| | October | 12th: Edward VI is born; 24th, Jane Seymour dies in childbirth |
| 1540 | | Elizabeth Blount dies |
| | January | 6th: Henry VIII marries Anne of Cleves |
| | July | 9th: Marriage to Anne of Cleves is annulled; 28th: Henry VIII marries Catherine Howard |
| 1542 | February | 13th: Catherine Howard is executed |
| 1543 | July | 12th: Henry VIII marries Catherine Parr; 19th: Mary Boleyn dies |
| 1545 | August | 24th: Charles Brandon, Duke of Suffolk, dies |
| 1547 | January | 28th: Henry VIII dies; Edward VI ascends to the throne |
| 1548 | | Catherine Parr marries Thomas, Lord Seymour of Sudeley |
| | August | 30th: Mary, daughter of Catherine Parr and Thomas Seymour is born |
| | September | 7th: Catherine Parr dies Etheldreda Malte marries John Harrington |
| 1549 | March | 20th: Thomas Seymour is executed |
| 1550 | | Thomas Stukeley is the King’s standard bearer in Boulogne |
| 1552 | | Katherine d’Eresby marries Richard Bertie |
| 1553 | July | 6th: Edward VI dies; 10th, Jane Grey is proclaimed Queen of England; 19th: Mary I ascends to the throne |
| 1554 | | Anne Bassett marries Sir Walter Hungerford |
| | February | 12th: Jane Grey is executed |
| 1555 | | Thomas Stukeley marries Anne Curtis |
| | October–November | Etheldreda Malte dies |
| 1557 | July | 16th: Anne of Cleves dies |
| | December | Mary Howard, Dowager Duchess of Richmond, dies |
| 1558 | | (?) Anne Bassett dies |
| | November | 17th: Mary I dies Elizabeth I ascends to the throne |
| 1570 | April | Thomas Stukeley retires to Spain |
| 1571–3 | | Sir John Perrot is made president of Munster, in Ireland |
| 1578 | August | 4th: Thomas Stukeley is killed at the Battle of Alcazar |
| 1580 | September | 19th: Katherine d’Eresby dies |
| 1582 | | John Harrington dies |
| 1584–8 | | Sir John Perrot is made Lord Deputy of Ireland |
| 1592 | September | Sir John Perrot dies in the Tower accused of treason |
| 1596 | July | 23rd: Henry Carey, 1st Baron Hunsdon, dies |
| 1603 | March | 24th: Elizabeth I dies |
