The first round of the English Monarchs FA Cup has 11 match-ups remaining.  For those who just come across this series, here’s an overview:

Sixty-four monarchs throughout English history have been randomly drawn against one another in the format of the football FA Cup. The winner of the match-ups progress through to the next round until the very best monarch in English history is declared.

The eighth part of the first round will focus on three fixtures:

  • Edward V v Oliver Cromwell
  • Edward the Confessor v Edward II
  • William III v Lady Jane Grey

Edward V (r: 1483)


Oliver Cromwell (r: 1653-58)


What’s this: a king killer and republican in the competition for the English Monarchs FA Cup? Isn’t this against the principle of this tournament, I hear you ask. Well, yes, if you were to raise such questions you would be entirely right. However, a year ago when this series started I struggled to get 64 entrants in order to have the right numbers, and rather than provide a bye for a couple of monarchs in the first round, I used a bit of artistic licence to incorporate Oliver Cromwell(and his son, Richard).  Ultimately, Cromwell did rule the country, and so has merit to be included. In this manner, I look upon the inclusion of the Cromwells in the same way I look upon the inclusion of Welsh teams in the English FA Cup – ultimately, in the grand scheme of things, it makes a bit of sense.

This series’ very first post of this series featured Oliver Cromwell’s son, Richard Cromwell; the younger Cromwell was trounced by Henry V. However, Oliver Cromwell is a completely different beast. As I noted above, he was a king killer (of Charles I), and so not someone to mess with. However, in many ways, Cromwell remains an enigmatic figure: someone who came to rule the country, but yet a man who many find hard to place.

His competition in this round, poor Edward V, fails to live up to such feats. Edward V is one of a few kings whose reign was so short that he was never actually crowned. The circumstances of this short reign of a handful of months in the summer of 1483 has been recounted elsewhere in this series; particularly the fixtures featuring Edward IV and Richard III. Edward was the victim in a wider tale of Richard III’s lust for the crown, and such was his youth that Edward was forced to be a by-stander in his own tale.

After his father’s death in 1483, Edward was taken into custody by his uncle, Richard (then Duke of Gloucester), and taken to London to be kept in the Tower (along with his younger brother, Richard, Duke of York). Ostensibly, this was for Edward’s own safety, however, as the days passed by Richard of Gloucester clearly plotted for someone more than mere protector of the new king: the crown for himself. All of this has been excellently (and misleadingly) portrayed in Shakespeare’s play Richard III, but ultimately the ambition and overall trajectory remains the same: Richard highlighted his own claim above his nephew’s. Firstly, the marriage of Edward IV to Elizabeth Woodville (Edward V’s parents) was declared illegitimate, and then after this the two young princes simply disappeared.

The “Princes in the Tower”mystery is a popular and well-established one. What became of Edward and his brother? Some theories note that they managed to escape (and the later pretender to the throne, Perkin Warbeck, claimed to be the younger prince), or that others did away with them (such as Margaret Beaufort, in order to raise the royal clam of her own son, Henry Tudor). But it is much more likely that uncle Richard did away with his nephews to prevent any future rebellion in their name.

Of course, Richard III did not reign for long – only two years – before Henry Tudor claimed the throne for himself at Bosworth in 1485. As regular readers may be aware, the fast-paced and action-packed events of 1483 is an area that I have touched upon a few times before. Earlier this year I posted a “What If…” scenario: what if Richard III actually won at Bosworth in 1485. In it I speculate that the ramifications of a Richard victory in 1485 could have meant a continuation with the wars against France (a Two Hundred Years’ War, perhaps) and how England could have remained a Catholic nation.

Richard III’s brief reign is of scant comfort to the doomed Edward V. He remains a boy king on which a harsh injustice was meted out. As such, he cannot possibly rival the achievements of Oliver Cromwell: a man who helped establish an English republic. The wildcard “not-actually-a-king” contender survives into the second round. Perhaps Cromwell will make a mockery of this entire competition by going on to win it!

Winner: Oliver Cromwell

Edward the Confessor (r: 1042-66)


Edward II (r: 1307-1327)


This post provides a second Edwardian derby, with the first coming in the form of Edward the Elder defeating Edward VIII. A few centuries set both of these Edwards apart, but both faced serious hurdles during their eventful reigns.

Edward the Confessor remains an intriguing monarch; his two decades long reign came in-between great disruption on the English throne. The kingdom had faced serious challenges and rivals prior to his succession, with the throne taken by the Danish royal line under Cnut the Great (r: 1015-1035). Edward managed to take the throne due to his royal blood and connections: he was the son of former king Ethelred the Unready, and via his mum (Emma of Normandy) he had links to the Danish kings who held the throne in the 1030s-40s.

Although his succession restored the old Anglo-Saxon royal house to the throne, his time in power was one in which the crown was severely weakened. The Godwins of Wessex grew in importance, and having attempted to banish them Edward was faced with their triumphant return in the 1050s. All of this shows the balancing act that Edward had to operate during these years: between upstart nobles and the envious eyes of foreign monarchs.

Edward’s death at the start of 1066 unleashed a chain reaction of events that established this year as one of the most important in English history. Harold – of the Godwins – claimed the throne, but was then challenged by the king of Norway (who he beat) and then William of Normandy (a battle in which he lost). The events of Harold’s short reign were recounted in an earlier post in the series; in many ways, these subsequent events demonstrate the skill in which Edward the Confessor navigated his reign.

What of Edward II? The majority of historians would undoubtedly classify Edward II as one of England’s worst monarchs. He had the misfortune to be sandwiched beside his father (Edward I) and son (Edward III), who could lay claim to be two of England’s most successful rulers. Furthermore, the years of his reign – from 1307 to 1327 – were filled with problems.

Some of these problems include failure in war with Scotland; never a good sign of an English king. His father was known as “the Hammer of the Scots”, but it was Edward who faced defeat at Bannockburn in 1314; this led to the re-establishment of the Scottish royal house under Robert the Bruce.

Perhaps of bigger importance was Edward’s reliance on close male friendships; initially with Piers Gaveston, and then in the 1320s with Hugh Despenser. These friendships were hated by the nobility and the tension led to the outbreak of rebellions (with poor Piers jettisoned and killed). Back in 2018 I covered the relationship between Edward II and Piers Gaveston (as part of research into the earls of Cornwall),  in which I outlined the rumour of their friendship:

Generation after generation of historians have debated the truth behind the relationship of Edward and Gaveston: was it a homosexual liaison, or a close bond between brothers-in-arms? To be honest, it is not a debate that I’m particularly concerned about; it is the impact of their relationship on politics and society that is the most intriguing.

Whilst reading into articles about Gaveston (thankfully I have a log-in to History Today) I came across J.S. Hamilton’s piece from 1999 ‘Meage a Roi: Edward II and Piers Gaveston’; in it he references a painting by Marcus Stone from 1872. It is a wonderful image in that it displays the affection between king and earl, as well as the jealously of the other barons (including what could possibly be Edward’s queen, Isabella):


By the mid 1320s the power of the crown had been sucked from Edward into the hands of his wife, Isabella, and her lover Roger Mortimer. He renounced the crown in 1327 in favour of his teenage son, and later died in the same year in Berkley Castle. It is more than likely that he was murdered, with a popular story noting how he may have suffered from a poker up his backside.

Both Edward’s faced severe problems throughout their reigns, and both were limited in terms of their freedom and ability to push forward the policies they wanted. However, when compared together, it is clear that the Confessor was more successful than Edward II. Most importantly, the Confessor was not ousted from the throne and forced to face a bloody end.

Winner: Edward the Confessor

Lady Jane Grey (r: 1553)


William III (r: 1685-1702)


William III is a monarch who has appeared on the pages of this blog more than just a couple of times. His landing in Torbay in 1688 is a highlight of local history from my area, and a history walk has been recreated several times by the History with English foundation degree team from University Centre South Devon. Previous posts have highlighted these walks (although unfortunately, with COVID-19, the 2020 edition will likely be cancelled or postponed).

Previous posts about William have provided an overview of his arrival in England in 1688:

The year is 1688 and James II sits on the throne of England and Scotland. However, problems are stirring: James is a Catholic and there are many in the country who do not wish to return to the religious upheaval of the Reformation period (yes, we’re looking at you Mary I). Leading bishops petitioned against James’ Declaration of Indulgence, which provided greater rights for Catholics in the country; however, James reacted by imprisoned several of them in the Tower of London (one of their number was the Cornishman Jonathan Trelawny). Many of the nobility feared James asserting his royal authority and acted swiftly; their anecdote was to call out to William of Orange to come to England to become the new king.

William himself had royal blood in his veins and was also married to James’ daughter (Mary), and most importantly of all: he was a Protestant. William didn’t need much convincing – the power of England would help the Dutch in their fighting against the much larger French – and so he readied his troops and headed for England. Brixham was the landing spot, and the day itself – 5th November – served as a good omen. Yet another Catholic plot was to be rumbled and the Protestants, it was hoped by many, would prosper yet again. William’s army numbered up to 40,000 and he marched from the west-country to London to seize the throne. Rather than meet his rival in the field of combat James II fled to the continent, leading to the start of the reign of William III – the so-called Glorious Revolution (if we are to buy into the Whig interpretation of history).

Once on the throne, William had an eventful few years in the hot-seat before dying in 1702. He used his new-found position to further his own Protestant beliefs in a series of wars, notably within the Nine Years’ War against France, and against the Catholic Irish. All of which provided his place in the history books, for better (to the merriment of the Orange Order) or for the worse (to the concern of those who admire religious toleration).

Lady Jane Grey, by comparison, did not achieve the same number of feats as William. Her actual listing as an English could be easily disputed: she has gone down in history as the “nine day queen”, and her reign – if we can call it that – completely failed to obtain the confidence and backing of the English people and political establishment.

1553 was the year in which Henry VIII’s son, Edward VI, died. It created a huge problem for politicians, notably the Duke of Northumberland (who had helped guide the young Edward during the early 1550s). The next in line to the throne was Mary, however, Mary was a woman (obviously!) and a Catholic (which went against the Protestant reforms of the past twenty years). Northumberland came up with a plan: the so-called “Devise for the Succession.”

The plan was simple enough: ignore the claims of Mary (and her younger half-sister, Elizabeth), and instead promote a different branch of the family tree: the Greys. Lady Jane Grey was married quickly to Northumberland’s son (Guildford Dudley), and it was clearly hoped that Jane and Guildford would be pliant and abiding to Northumberland’s wishes. One of Edward VI’s dying acts was to sign the devise.

At this point Mary had two options: run or fight. Many believed that she would flee to the safety of fellow Catholics on the continent, however, Northumberland and others did not fully take into consideration that the blood of the proud and energetic Henry VIII flowed through Mary’s veins. She stood her ground and sounded out her own rightful claim to the throne. As such, the forces at Northumberland’s control vanished, and the political establishment ignored the devise and put their full support behind Mary. Such a move was recounted in an earlier round of this series, in which Mary defeated Stephen to earn a place in the second round.

Northumberland was executed for his treachery in 1553. Lady Jane Grey and her husband were locked in the Tower; however, after the disturbances of the Wyatt Rebellion in 1554, both were also executed. In this manner, it would be easy to view Jane as one of history’s losers. Her elevation into the spotlight and subsequent killing is a tragedy of the Tudor period. She was a victim of the ever turning spinning carousel of political deceit and lies of this era.

And so, William III joins his wife – Mary II– in obtaining a place in the second round of the competition. He is well-placed to go far in the competition. Let’s see how far he can sail onward, perhaps with the aid of the so-called “Protestant Wind”.

Winner: William III

The results so far:

  1. Henry V beat Richard Cromwell
  2. Edmund Ironside beat Henry VI
  3. Edward III beat Richard I
  4. Elizabeth beat Cnut
  5. Victoria beat Henry I
  6. Elizabeth II beat George VI
  7. William IV beat Louis
  8. James I beat Edward VI
  9. Eadred beat Harold
  10. Henry III beat Edward IV
  11. Henry IV beat Sweyn Forkbeard
  12. George III beat George I
  13. Mary I beat Stephen
  14. Matilda beat Charles I
  15. Edward the Elder beat Edward VIII
  16. Edgar the Peaceful beat Eadwig
  17. Edmund I beat Richard III
  18. Aethelstan beat John
  19. Mary II beat Harold Harefoot
  20. William the Conqueror beat Aelfweard
  21. Henry II beat Ethelred the Unready
  22. George II beat William “Rufus” II
  23. Oliver Cromwell beat Edward V
  24. Edward the Confessor beat Edward II
  25. William III beat Lady Jane Grey