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| 1650 | Battle of Dunbar |  |
| 3rd Sep Dunbar Helps Cromwell defeat the Scottish Army |
| 1650 | Invasion of Scotland | |
| 28th June Crosses the Scottish border with an invasion force led by Cromwell |
| 1651 | Battle of Worcester | |
| 3rd Sep Worcester Forces Charles II's Scottish allies back into the confines of Worcester |
| 3rd Sep Worcester Leads a Parliamentary force across the River Teme prior to the Battle of Worcester |
| 1651 | Mobilization | |
| 27th Aug Evesham Joins forces with Cromwell, 15 miles sth west of Worcester, a combined force of 28,000 |
| 1651 | Siege of London | |
| Aug London Prepares the defences of London after Charles II leads an invasion force into England |
| 1652 | Act of Settlement | |
| The chief feature of the administration is the implementation of the Act of Settlement 1652, which decreed the settlement of the New Model Army's soldiers on the confiscated estates of Catholic landowners |
| 1652 | Commander | |
| Appointed Commander-in-Chief in Ireland |
| 1652 | Cromwellian Settlement | |
| Appointed Lord Deputy of Ireland, where he enforces the Cromwellian Settlement |
| The first year of his tenure sees the mopping up of the last Catholic Irish guerrilla resistance to the Cromwellian conquest of Ireland |
| 1652 | Lord Deputy of Ireland | |
| Appointed Lord Deputy of Ireland, where he enforces the Cromwellian Settlement |
| 1652 | Marriage | |
| Marries Cromwell's daughter, Bridget, widow of Henry Ireton |
| 1652 | Rebellion | |
| Fleetwood negotiates with the remaining guerrilla bands (known as "tories") to either surrender or to leave the country for service in the army of a country not at war with the Commonwealth of England |
| The first year of his tenure sees the mopping up of the last Catholic Irish guerrilla resistance to the Cromwellian conquest of Ireland |
| 1652 | Rule of Ireland | |
| Appointed Lord Deputy of Ireland, where he enforces the Cromwellian Settlement |
| The chief feature of the administration is the implementation of the Act of Settlement 1652, which decreed the settlement of the New Model Army's soldiers on the confiscated estates of Catholic landowners |
| 1653 | Rebellion | |
| The last organised Irish force surrenders in 1653 |
| 1659 | Parliament | |
| General Charles Fleetwood demands indemnity for the Army & arrears of pay & a return to republican rule |
| General Charles Fleetwood leads a mutiny of the Army |
| 25th April The republicans in Parliament allied with the army forced Richard Cromwell to dissolve Parliament |
| 1659 | Rebellion | |
| General Charles Fleetwood demands indemnity for the Army & arrears of pay & a return to republican rule |
| General Charles Fleetwood leads a mutiny of the Army |
| 25th April The republicans in Parliament allied with the army forced Richard Cromwell to dissolve Parliament |
