| From | To | Event |
| 1066 | | William I the Conqueror |
| 1189 | | Richard I Coeur de Lion |
| 1216 | | Henry III |
| 1220 | | Halley's Comet |
| 1270 | | Eighth and last Crusade |
| 1272 | | Edward I Longshanks |
| 1297 | | Halley's Comet |
| 1307 | | Edward II |
| 1327 | | Edward III |
| 1337 | | 100 Year War begins |
| 1373 | | Halley's Comet |
| 1377 | | Richard II |
| 1399 | | Henry IV |
| 1400 | 1499. | Muslim east coast trade as far south as Sofala |
| 1413 | | Henry V |
| 1422 | | Henry VI |
| 1455 | | Wars of the Roses |
| 1456 | | Halley's Comet |
| 1461 | | Edward IV |
| 1470 | | Henry VI |
| 1471 | | Edward IV |
| 1483 | | Edward V |
| 1483 | | Richard III |
| 1485 | | Henry VII |
| 1488 | | Bartolomeu Dias reaches beyond Mossel Bay, named Angra dos Vaqueiros - Bay of Cowherds - with reference to Khoekhoe herders seen on shore |
| 1492 | | Columbus discovers America |
| 1498 | | Vasco da Gama rounds Africa |
| 1503 | | Antonio de Saldanha lands at Table Bay |
| 1505 | | Portuguese take over Sofala |
| 1509 | | Henry VIII |
| 1522 | | Magellan circumnavigates the World |
| 1531 | | Halley's Comet |
| 1547 | | Edward VI |
| 1553 | | Jane |
| 1553 | | Mary |
| 1558 | | Elizabeth I |
| 1603 | | James I |
| 1605 | | Guy Fawkes Gunpowder Plot |
| 1606 | | Australia discovered |
| 1607 | | Halley's Comet |
| 1618 | | 30 Year War begins |
| 1620 | | Pilgrim Fathers arrive in Amarica aboard the Mayflower |
| 1625 | | Charles I |
| 1642 | | English Civil War |
| 1642 | | New Zealand discovered |
| 1649 | | Charles II |
| 1652.04.06 | | The first white settlers, led by Jan van Riebeeck, arrive in Table Bay. The Cape Colony is governed by the Dutch East India Company(VOC)until 1795. |
| 1654 | | Asian convicts brought to Cape as slaves. |
| 1656 | | Catharina Anthonis, a slave born in Bengal, was the first slave to be freed, because Jan Woutersz wanted to marry her. |
| 1657 | | Settlement in Liesbeeck Valley (Rondebosch) by first 9 free white burghers. Slaves imported from Madagascar and Java. |
| 1657 | | First Free Burghers settle on Khoekhoe land |
| 1658.03.28 | | 38 male slaves and 37 female slaves from Angola, arrive in Table Bay aboard the Amersfoort. |
| 1658.05 | | 228 slaves from West African coast arrive in Table Bay aboard the Hasselt. About 80 are shipped to Batavia. |
| 1659 | 1660. | Armed Khoekhoe resist Dutch seizure of land |
| 1660 | 1679. | Expansion of Cape settlement |
| 1660 | | Almond hedge planted to protect the settlement from the Hottentots (Khoikhoi). First horses arrive at the Cape from Batavia, circa 1660s. |
| 1660 | | Charles II |
| 1661 | | Rumours noted at Cape concerning "Briqua" - later known to be Tswana |
| 1662.05 | | Jan van Riebeeck leaves the Cape for Malacca. |
| 1662 | | William III |
| 1663 | | Outposts set up at Saldanha Bay and Hottentots Holland. |
| 1664 | | Great Plague of London |
| 1665 | | The first Dutch Reformed Church congregation founded at the Cape and the first minister appointed, Rev. J. van Arkel. |
| 1666 | | The Castle (or Fort) building started in Cape Town. |
| 1666 | | Settlements in Saldanha Bay and Vishoek (Fish Hoek). First Calvinist church built in Cape Town. |
| 1666 | | Great Fire of London |
| 1667 | | Indians arrive at the Cape. |
| 1673 | | Second Dutch-Khoekhoe war |
| 1678 | | Settlement of Hottentots-Holland. |
| 1679 | | Simon van der Stel arrives with orders to expand colony |
| 1679 | | Stellenbosch founded. Castle in Cape Town is completed. First farmers settle along the Eerste River. |
| 1682 | | Halley's Comet |
| 1685 | | Simon van der Stel visits Namaqualand |
| 1685 | | Commissioner Hendrik van Reede (VOC) decrees that male slaves can buy their freedom for 100 guilders on reaching the age of 25 years, provided that they have been confirmed in the Dutch Reformed Church and can speak Dutch. |
| 1685 | | The same conditions apply to female slaves, who can buy their freedom at age 22 years. |
| 1685 | | James II |
| 1686 | | Dutch Reformed Church congregation founded in Stellenbosch. |
| 1687 | | Settlements along Berg River (Drakenstein, Paarl). |
| 1688.04 | 1689. | Approximately 200 French Huguenots arrive at the Cape, settle mostly in Fransch Hoek. |
| 1690 | 1699. | Trekboer class emerges |
| 1691 | | Dutch Reformed Church congregations founded in Drakenstein and Paarl. |
| 1694 | | William III |
| 1698 | | Settlement of Wagenmaker's Vallei (Wellington). |
| 1700 | 1799. | VOC slave trading in Mozambique; Zanzibar and Madagascar |
| 1700 | | Settlement in Land van Waveren (Tulbagh). |
| 1701 | | Cattle raids by Khoisan commence against Dutch |
| 1702 | | Anne |
| 1713 | | Smallpox epidemic in the Cape, introduced from India, decimates Hottentots, kills many whites. |
| 1714 | | George I |
| 1717 | | System of freehold title to land ends, by which time about 400 farms granted. |
| 1720 | 1749. | Western Cape Khoekhoe reduced to labouring class |
| 1722 | | Groot Constantia is built. |
| 1727 | | George II |
| 1730 | | The VOC imports slaves from Mozambique and Zanzibar. First Boers reach George area, trek inland into Langkloof. |
| 1732 | | Annual rental of a leningplaats doubled to 24 rixdollars. Quitrent system of land tenure introduced. |
| 1734 | | Great Brak River proclaimed eastern boundary of Cape. |
| 1737 | 1743. | Short-lived Moravian mission to Khoekhoe |
| 1743 | | First recorded Trekboer loan farms in Roggeveld |
| 1743 | | Dutch Reformed Church congregations founded in Roodezand and Tulbagh. |
| 1745 | | Dutch Reformed Church congregations founded in Swartland (Malmesbury). |
| 1746 | | Swellendam is founded. |
| 1754 | | First recorded |Xam San resistance to Roggeveld Trekboers |
| 1755 | | Smallpox epidemic in the Cape. Foundation stone of Old Town House in Cape Town is laid. |
| 1758 | | Halley's Comet |
| 1760 | | Jansz; Coetse with Klaas Barends and others cross Gariep River |
| 1760 | | George III |
| 1761 | 1762. | Hendrik Hop travels to Gariep River |
| 1765 | | 112 slaves from Madagascar arrive in Table Bay on board Meermin. |
| 1770 | | Mothibi son of Molehabangwe of Tlhaping born at Nokaneng |
| 1770 | 1799. | Intensive Khoisan resistance to Trekboer occupation |
| 1771 | | Clashes between Trekboers and Xhosa begin as trekkers cross the Gamtoos River in the east |
| 1773 | | Boston Tea Party |
| 1774 | | General Commando mounted against San: 503 killed; 241 captured |
| 1775 | | American War of Independance |
| 1778 | | Colonial boundary extended to Buffels; Zak; and Fish Rivers |
| 1778 | 1779. | Hendrik Jacob Wikar and Robert Jacob Gordon meet Khoekhoe; Geisiqua and Tswana groups along lower and middle Gariep which Gordon names Orange River in honour of the Netherlands Stadtholder |
| 1780 | | First Frontier War between Xhosa and whites. |
| 1782 | | First issue of paper rix dollars. |
| 1783 | 1792. | Le Vaillant and Van Reenen travel in Namaqualand and north of Orange River |
| 1786 | | Graaff-Reinet founded. |
| 1789 | | Merino (wool-producing) sheep brought from Holland |
| 1789 | | French Revolution - republican sentiments spread |
| 1789 | | Merino sheep imported from Holland. |
| 1789 | 1793. | Second Frontier War between Xhosa and whites. |
| 1790 | 1799. | In documented raids on "Bosjesmen" 2000 - 3000 Khoisan are killed |
