The unfinished business of Bosworth 1485

[Here follows a fictitious account that examines the 'what if' of both King Richard III and Henry Tudor surviving Bosworth 1485. The royal army had routed, but Richard was still alive and the legitimate king, while Henry remained a significant threat with an army in the field that has tasted victory once already! ]

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 75 - 100 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.

 

9th September.

Richard’s army left York in a grand procession surrounded by music and cheering crowds. For a recently defeated king, he was in high spirits and the morale of the army was good.

His planned route was to be made via Doncaster, down the north / south road,  leaving the main route road at Spink Hill and moving on down through Chesterfield, Derby and Tamworth, allowing the army to approach Coventry from the north west, avoiding Nottingham altogether. This approach brought its own perils as the area around Derby was under Stanley influence and Richard doubted that his army could move here without Stanley being promptly informed!

 

13th September

Richard reached Doncaster, his approach was observed by Henry’s light cavalry, who promptly withdraw to shadow Richard, while sending fast riders back to Henry to advise him.

Elsewhere, Thomas Holmes, acting as herald, was carrying an instruction from King Richard for John de la Pole (Lincoln) in London, to bring forces to Coventry by the 19th September.

Holmes had already been delayed once at West Rottington due to the presence of Lord Trebian’s Lancastrian patrols. Now he was delayed again at St. Albans, just 20 miles outside London, but this time he was rumbled and detained.

Under questioning he revealed the stated aim of his mission. Fast riders were sent to warn Henry, who was still at Nottingham (100 miles away).

14th September

Once Henry received the news that Richard had reached Doncaster, his army began their march to meet him, by the end of the day, reaching the monastery Felley Priory. Richard was at Bramley (just 30 miles apart).

16th September 

On hearing the report from St. Albans, that the royal army intended to gather at Coventry on or about 19th September, Henry now knew not only where Richard was, but where he was going to.

He could not allow that rendezvous to occur, a reinforced royal army might spell disaster for his respectably sized force of 12,000 men. He decided to deal with Richard immediately and then turn back south to face the southern Yorkists gathering at Coventry. 

By the end of the day, his army, moving north, was approaching Bolsover. Reports were coming in that Richard’s army was just 8 miles away at Spink Hill. The area was pro-Lancastrian, with his uncle, Jasper Tudor having title to the land.

With the approach of night, Richard had set up camp on Spink Hill. His patrols returned with news that Henry was nearby. How unlucky, he had just narrowly missed avoiding Henry altogether. If he would have had just 24 hours march on Henry, he would likely have been ahead of him, passing  Chesterfield and on the way to Derby. Instead, Henry’s army was too close and in the morning there would be fighting. Another chance perhaps, to once and for all, settle this festering civil war. 

The armies would meet at Oxcroft, a featureless, farmed plateau, with its crop of peas, beans and late barley, still being lifted.

17th September 1485 - the armies approached each other, this battle would over-shadow Bosworth in its significance ….. the Battle of Oxcroft Field! (See Resource Section)

Resource Section.

The Blog post that covers the Battle of Oxcroft Field - LINK

https://battlefieldswarriors.blogspot.com/2026/08/the-battle-of-oxcroft-field-17th.html

There is a post covering the Bosworth scenario on the blog, which describes the essential elements of the scenario and gives a brief AAR … events there have brought us to Oxcroft. 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