The unfinished business of Bosworth 1485

[Please note, this is an ongoing post that will be added to. It tells the tale of post Bosworth manoeuvres. How will this power struggle between Richard and Henry be concluded. If you like this sort of thing, please call back over the next few days and check on progress, which will be added in chronological order].

In the Year of our Lord 1485, in the Parish of Dadlington, Richard, our most noble king was sorely put to test by Henry Tudor, aided by the treachery of the Stanleys. With troubled days ahead, only loyal hearts can save all.

22nd August 1485

Bosworth battlefield lay strewn with the dead and the dying. The Lancastrians under Henry were victorious, but Richard III, the legitimate king was still alive. 

Towards the end of the battle, he had observed Sir. William Stanley send contingent after contingent of billmen over to Henry’s position and sensing that the odds were now heavily stacked against him, he heeded the advice of those around him and withdrew from the field with his body of horse.

Politically, he needed to be in London (south), but militarily, the moment called for him to move towards his northern strongholds. First he much catch up with Lord Percy (Northumberland), who just hours before had retired from the battlefield without becoming involved in the fighting - if nothing else, Northumberland’s force was at least fresh, offering some security if pursued.

There was of course the question amongst Richard’s party as whether Northumberland could be trusted, but Richard, ever the pragmatist, knew that if he was to defeat Henry and the rebellion, then he must galvanise his northern support, not divide them. He was also somewhat accommodating to the fact that had Percy become involved in the fighting, his force would have been at least roughly handled and more likely destroyed, better to have Percy as a significant cadre to build another army around.

Choices for Henry were a little less clearcut. He was grateful for Sir. William Stanley’s intervention, but vexed that his support had only become so obvious, late in the battle. Of more immediate concern was why Lord Stanley had chosen not to show his support more demonstrably, but diplomatically he accepted the excuse that Stanley had been guarding the rebel flank from a possible manoeuvre by Northumberland.

Never-the-less, Henry was reluctant to send the Stanleys and their fresh cavalry in headlong pursuit of the fleeing Yorkists …. he wanted them on a tight leash for now! Not that the Stanleys had any hope of convincing Richard that they were still loyal to the crown - those bridges had been well and truly burned!

Instead, Henry sent off Sir. John Savage and his light cavalry to follow the retreating Yorkists and establish their movements and intentions

In due course, Henry would follow, taking the army to Nottingham, a Yorkist stronghold and a days march away. He believed Richard would retreat to that position and attacking him early, before he could recover his strength had obvious advantages. In any case, Nottingham, was a central location, if Richard had escaped him, from there Henry could strategically move either north or south as the situation dictated.

First, he needed to rest and re-supply his army. He sent heralds to the major population centres to give the news that Richard and the royal army had been defeated in battle and actively went about recruiting, hoping to persuade those who had hesitated in joining the rebellion, to do so now.

Time was not on Henry’s side, his war chest courtesy of the King of France (Charles VIII), still had funds, for now, so he could continue to pay his French mercenaries and of course to others, he could make promises of titles once the crown was his!

1st September 1485

Ten days later, rested and re-organised, Henry had learned that rather than falling back on Nottingham (central England), Richard had moved North, with York being his likely destination.

Henry’s ranks were starting to fill with persons of note declaring their support. He was ready to start moving. 

The French and Scottish mercenaries under Philibert de Chandée would form the vanward, John de Vere 13th Earl of Oxford, reinforced by Edward Courtenay, Earl of Devon, took the mainward and the Stanleys were entrusted with the rearward.

In Henry’s most trusted circle was his uncle, Jasper Tudor, Earl of Pembroke. He would command a small reserve of 200 mounted men-at-arms. The total size of his force at this time was around 12,000 fighting men.

Henry voiced that this force, which would likely grow while marching, was strong enough to take control of London, from where he would have access to the Royal Treasury and operate the levers of power, such as denying Richard of tax revenue and in particular calling Parliament to consider Richard being declared a traitor.

Philibert de Chandée instead advised that Henry move north towards York and deal with Richard quickly by bringing him to battle (again). His caution lay in the question of how easy it would be to practically control London while King Richard was still at large. ‘We shouldst cutteth off the vip'rs headeth’.

Both Oxford and Jasper Tudor agreed with the French commander. However, the Stanley’s felt that the London option was the best, but Henry read their eagerness as the Stanleys reverting to a ‘hedging of bets’ stance, typified by them avoiding a commitment to conflict whenever possible and his mistrust immediately encouraged him to put his authority behind the decision to seek Richard out for battle. They would march north!

5th September 1485

Richard was both grateful to see the degree of potential support that remained loyal to him, but personally frustrated by virtue of his impatience at wanting to start the march south now, but he had heeded the warning of Viscount Lovell that the army was not yet ready.

The harvest was still being brought in and so the magnates had fewer men to spare than might otherwise have been the case.

Richard lost most of his guns at Bosworth, but had managed to secure a small artillery train from northern nobles and local town arsenals, though a little time was needed for them to be assimilated into his army.

At a Council of War, it was agreed that the army should, if possible, avoid an engagement with the rebel army until such time that support from the south had joined the ranks of the royal army. With Henry likely to control the north/south road at Nottingham, they settled on Coventry as being the most practical rendezvous point for two weeks' time … 19th September. 

To make Coventry for that date, Richard’s army would need to start the 120-mile march in four days' time, on the 9th September, the 11th at the latest if the weather held. There was a renewed urgency in preparations.

Percy (Northumberland) would take the vanward, reinforced by additional bowmen from Viscount Lovell’s contingents. Richard would take the mainward and John de la Zouche  the rearward. Confidence amongst the royal army was slowly being restored. It was time to take the fight to Henry.

6th September

Henry’s army had marched the 35 miles to Nottingham, an important position in central England, that governed the north / south movement between York and London. He was convinced that Richard would only have one of two objectives in mind, Nottingham or London. From here, Henry could intercept that expected approach.

He now needed to know where Richard was. He was certain that the impulsive king might already be on the move to Nottingham. Light cavalry were sent up the northern road to Doncaster (50 miles away), with instructions to report back on any enemy movement.  

Unbeknown to Henry, at the moment, the royal army was of course still in York, making final preparations to march.

7th September. 

As Henry’s cavalry pushed hard to get to Doncaster, they reached the Hamlet of Piggy Longton, in the Parish of Dungborough, estates controlled by the Yorkist, Lord Darcy (above photo).

Here they met determined resistance from Darcy’s Household and leaving several dead behind, they were forced to retreat. Denied the bridge crossing at the Smoggy Brook, they were forced into making a long detour to reach the safety of West Rottington, on the estates of Lord Trebian, a loyal Lancastrian, where they rested their horses and tended to the wounded, before pressing on for Doncaster. 

More to come ***************

Resource Section.

There is a post covering the Bosworth scenario on the blog, which describes the essential elements of the scenario and gives a brief AAR … which leads us to this journey. LINK;

https://battlefieldswarriors.blogspot.com/2026/07/bosworth-scenario-building.html

My sister webspace ‘COMMANDERS’  showcases the various figure and boardgame systems that I am enjoying and gives a flavour of where current projects are up to. Link;

https://commanders.simdif.com/dear_diary.html

Bosworth - scenario building

I have put together a Battle of Bosworth 1485 scenario. It zooms in to the main part of the action and assumes that some fighting and manoeuvre has already occurred. It makes the decision to leave some formations out of the game and as a consequence is a tad kinder on smaller collections. 

The following is a discussion of why it looks like this, followed by an AAR of a first run out with it.

There are a few resources at the bottom of this post that link back to some posts that have already tackled the Bosworth subject and since they exist, I will not be covering some of that old ground here.

We are taking into account information that is post 2009, when the true location of the battlefield was identified. The scenario has been written within the terms and mechanisms of the 'Test of Resolve' rules, which I am presently favouring.

I should say that much of what I have put together accords with the Bosworth scenario that the Test of Resolve team have put in their own scenario.

In the main, I have been referencing three books; Osprey’s Bosworth 1485 - The Downfall of Richard III by Christopher Gravett (not his earlier Osprey book on the same subject), Helion’s Richard III and The Battle of Bosworth by Mike Ingram and Pen & Sword’s Bosworth - the Archaeology of the Battlefield by Richard Mackinder.

We are starting the scenario part way through the battle and so some assumptions are being made. The key aspects of the design choices are as follows;

Oxford (Lancastrian main body) and Norfolk (Yorkist main body) are already in mid clash. Their archers have done their arrow thing and have now run back to the rear of their melee troops to support the clash of the melee troops!

Effect - the start positions show the melee retinues already in contact. A die roll is made for every Oxford and Norfolk unit to assess their losses up to this point. There is an uplift on the Yorkist die roll of +1 because they had historically been getting the harder time of it. 

Northumberland (Yorkist rearward) has already started moving away from the battlefield without making any intervention on Richards behalf. He will not appear in the game.

Artillery (both sides) The guns are positioned outside of the zoomed in area that we have chosen to represent. They have already been in action as the armies approached each other, raking into the flanks of Oxford and Norfolk. They are in the main not mobile enough to reposition themselves within our time frame to find new targets that are not blocked by friends (Richard had an advantage in artillery, he could have sorely done with them being in a different position to counter the French threat). They will not become involved in the game.

Lord Stanley is assumed to stay out of it. He is generally judged as being a commander who hedged his bets on which side to join, but evidence suggests he has already given the nod to supporting Henry. Either way, he did not intervene, so he is not represented.

Sir. William Stanley was positioned closer to Henry. He mostly stayed out of the action, but in the last moments of battle, when Richard moved against Henry directly, he did send his men forward to assist Henry and it was likely his men that cut Richard down.

Effect - Sir William is off board, but once the Yorkist event card goes into the draw deck allowing Richard to directly charge Henry, then at the same moment, the Lancastrian event card will also be put into the deck that will allow up to two of Sir William’s melee retinues to attach themselves to Henry. The consequences are then hostage to the card sequence of play as to whether Richard can reach Henry and kill him before Henry becomes reinforced and it gets harder to do that.

It appears that the French contingent (includes Scots) that Henry brought with him when he landed in Wales, has not been given the recognition in Tudor accounts that they deserve, feeding into a narrative that they were simply part of Oxfords line. Ingram elevates their involvement as being a fully independent battle that skilfully appeared on the Lancastrian left flank, surprising Richard and threatening to roll up Norfolks battle. Ingram goes on to give the French mercenaries the status of being the Lancastrian vanguard (not Oxford).

This is likely based around the source of Jean Molinet, who wrote about the battle five years later in 1490. He was a continental and a professional historian. He was not present at the battle, but took eye witness accounts from the soldiers returning to the continent. As a source, he might be valued as offering a counter to the Tudor propaganda machine and so I have chosen to give some weight to his account, accordingly the French and Scottish contingents have a significant role.

Effect - the French threat is very real and Richard will likely become compelled to use his own battle to deal with the French attack, rather than perhaps being free to choose to move forward and support Norfolk to stand against Oxford. Again we have a race, can Richard re-orientate and engage the French before they advance on Norfolk, tipping him over the edge.

Note - since playing the scenario, I have reduced Richard’s foot melee retinues from 3 to 2 as he actually had limited numbers of foot with him. This will add a bit more tension for the Yorkists, so that if things start getting tight, they will increasingly hope to be able to charge Henry directly, elevating the importance of that event.

Ingram and Gravett disagree on the orientation of the two armies, however they both agree that the marsh was on Oxford’s right and so the effect is that Oxford’s frontage is restricted in length, but so is the Yorkist army where it contacts the Lancastrians and the effect of that is that Richard will not be able to bring his overwhelming numbers to bear early in the fighting. Gravett has Northumberland on Richard's far left. Ingram has him located behind Richard, so that the Yorkist are deployed in depth. Neither matters as we have discounted Northumberland from the battle. The road doesn’t matter and it is being left out, so in effect, orientation is not a thing for us to worry about today.

The cavalry Swan Song - Richard charges Henry with a couple of hundred mounted household (classed knights or superior in the rules). This was due to some desperation on Richard’s part, a sort of do or die moment. I have called the scenario ‘This day I will die as a king or win’, these words uttered to the foreign leader Salazar, who urged Richard to escape. So we have this important element that Richard is determined to see this through, yet we must also acknowledge that the charge may not have been possible if the gap had not existed. However, I wanted to help the possibility of this important moment occurring (like the official Test of Resolve scenario does).

Effect - Once Richard's army loses two retinues, the Yorkist charge event card is placed in the card discard pile, at the same time, the Lancastrians place their Sir. William event card in the discard pile. Next turn onwards, the order that the shuffled cards are drawn may bring about the  famous charge and the reinforcing of Henry by Sir. William’s men running to his aid, in either order, or perhaps not at all. [note to those not familiar with the system, there are two End of Turn cards, when the second is drawn, all the cards are re-shuffled into a new draw deck …. So anything can happen and in any order. Can Richard deal with Henry before Sir. William’s men intervene!

Winning - obviously if there is only one survivor in the Richard / Henry exchange, then the survivor wins, the crown will be upon their head. Regardless of that, a game also ends immediately that a side loses six units. 

This supposes that if the Yorkists lose that many units, it will mean a collapse of their army (Northumberland has already gone), the Lancastrians will be too numerous and organised well enough so as to ensure that Henry’s physical position is safe, plus both Lord Stanley and Sir. William Stanley will likely have shown their hand in favour of Henry, further putting the remnants of the Yorkist army at risk. Richard will have been out-manoeuvred, but will still be king …. So who knows what would  happen then!

All of this has been taken into account in version 1.2 of the scenario. I have made this available in my Google Drive, link below in the Resource section.

Our refight - (using V1.1 before the latest update) 

 

At start, casualties at set-up are assessed. Oxford suffers 4, Norfolk suffer 5.

Above - Oxford and Norfolk engage, with archers supporting. The French and Scots are off photo, to the left (flank).

In response to the danger posed by the French, Richard begins to send his infantry melee retinues across to deal with them. The French crossbow are already hitting the Yorkist archers in the rear of Norfolks line.

Above - Richard's Billmen advance towards the French and Scots, having already driven their hand gunners in.

In the Oxford / Norfolk engagement, fighting is intense and two out of Oxford’s four melee retinues rout!

The first of Richard’s melee companies reach the French handgunners who flee to the rear of their billmen for safety.

Two of Richard’s Billmen companies reach the French Billmen. Richard’s third company is following, it should surely move against the French crossbow …. but, I have one of those delightful moments in a game, as to being vexed about what to do for the best, since Norfolk is also desperate for support. 

After pondering, Norfolk gets the vote! Fortunately for Richard, the fight against the French billmen is going very well and they are routed. For now, the French must forget about their flank attack against Norfolk, they are fighting to fend off Richard’s melee retinues.

The Oxford / Norfolk engagement is now getting to a critical point, both sides are very brittle, but it is Norfolk who has the fewest Battle Morale Points remaining - he cannot afford further loss!

Above - Richard from his commanding position is looking for Henry's banner!

There is tension in the battle as Richard sends out light cavalry to pinpoint Henry’s position ( this is a notional sending out of scouts, he is just desperately hoping his event card is drawn :-) )

In the French position, their pikemen get to drop on Richard’s billmen by striking them in the flank …. but (in the most unlucky of die rolls) the pikemen are repulsed! It is a moment that may come to define the battle.

And then it happens …. Norfolk takes a loss that crashes his Battle Morale, he goes on to fail his Test of Resolve and his battle disperses … all those units go to the ‘dead pile’ and the Yorkists have now lost at least ‘six units’, so the Yorkists immediately lose the game.

Sadly, we didn’t get to see a Richard on Henry fight, I checked the card draw deck and both of those event cards just happened to be  at the very bottom part of the draw pile, they could so easily have been near the top (or split, one at the top and one at the bottom) and Richard may have slain Henry and got rid of his rival, winning the game, or Richard himself may well have died, but such is the way of these things, we play for the fascination that uncertainty brings.

Above - this is what the Richard / Henry fight might have looked like.

So what does that mean now? We can assume that the Yorkist army is in rout, but the Yorkist king is still alive and has reluctantly escaped.

We will certainly need to fight another battle somewhere in the country. A sort of Bosworth II, perhaps the Random Battle Generator from the ToR rules could help with that. 

In this subsequent fight, more Lords may come to Henry’s cause, certainly the Stanleys will be at his side in the next fight. What of Northumberland? Historically, Henry imprisoned Northumberland for a short time, suggesting that Lord Percy had not made any agreement prior to battle to help Henry, so perhaps he will still fight for Richard and perhaps he might even have his own event card that could have him switch sides (or not) at the next battle, who knows! 

Richard’s authority is now deeply harmed, it is in the interest of all the Lords to now declare their ‘loyalty’ to someone, because whoever wins the next battle is going to remember who was loyal to whom …. will it be York or Lancaster!

I enjoy all of my gaming, but this has been a particularly enjoyable couple of hours of fun. The rules worked well and the situation seems to have enough nuance in it, that both sides have a fair chance, with good narrative falling from play.

It will get another playing and the scenario might get a bit more tweaking. The first version has nine items of red pen marked upon it already, so hopefully V1.2 will get us closer to 22nd August 1485. We shall see.

Resources;

A download of the scenario PDF V1.2  LINK

https://drive.google.com/file/d/1uBnpCDD_yfYNhXfW-TSafVsLweypv04W/view?usp=share_link

A previous post that discusses two different position proposals of the two armies. LINK

https://battlefieldswarriors.blogspot.com/2021/05/bosworth-1485-percy-attacks.html

A recent post that looks at the Christopher Gravell’s take on the new evidence. LINK

https://battlefieldswarriors.blogspot.com/2026/07/bosworth-reading-and-scenario-design.html

My other bit of webspace ‘COMMANDERS’ that is more snippet based than here and gets updated more regularly. LINK  

https://commanders.simdif.com/dear_diary.html