| Ruler | Country | Start of Reign | Age at 1500 |
| Henry VII | England | 1485 | 43 |
| 1501 | Tournament at the Tower of London  | | 1503 Feb | Elizabeth of York dies  | | 1503 Jun | Henry VII escorts Margaret to Scotland  | | 1503 Aug 8 | Marriage of James IV and Margaret  | | 1505 | Papal dispensation  | | 1507 | Thomas Wolsey becomes royal chaplain  | | 1509 Apr 21 | Death of Henry VII  |
|
| Henry VIII | England | 1509 | 9 |
| 1502 Apr | Prince Arthur dies  | | 1502 Oct | Henry becomes Duke of Cornwall  | | 1503 Jun 23 | Henry and Catherine's marriage arranged  | | 1505 | Papal dispensation  | | 1509 | Thomas Wolsey becomes royal almoner  | | 1509 Jun 11 | Henry marries Catherine of Aragon  | | 1509 Jun 24 | The coronation of Henry VIII  |
|
| James IV | Scotland | 1488 | ? |
| Louis XII | France | 1498 | ? |