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1369-1424, Scottish nobleman, called Tyneman [loser]; 2nd son of Archibald Douglas, 3rd Earl of Douglas. 

In 1390 he married Margaret Stuart, daughter of Robert III. He held Edinburgh against the English when Henry IV invaded in 1400. In 1402 Douglas was tried and acquitted of the murder of David Stuart , Duke of Rothesay, heir apparent to the throne. Later that year Douglas led a Scottish army against the English and was taken prisoner by Sir Henry Percy at Homildon Hill. 

He was then induced to join the Percy conspiracy against Henry IV, but at the battle of Shrewsbury (1403) he was taken prisoner by Henry and held until ransomed in 1408. 

From 1412 to 1422, Douglas continued his border warfare against England and was a member of several delegations of Scottish nobles who tried, unsuccessfully, to ransom their young king, James I , from the English. 

In 1423 he and his Scottish contingent joined the French against the English. He was made lieutenant general of the French army and Duke of Touraine. In 1424 the allies were defeated at Verneuil, and Douglas was slain.

2nd version:

In 1402, Douglas and his forces were defeated at Homildon Hill by Henry Percy (Hotspur). The two leader became such good friends that Douglas rode with Hotspur to Shrewsbury

Fought against King Henry IV of England at Shrewsbury. Achibald, bent of extermination of the King, hunted the field ruthlessly for the monarch. King Henry, for his own security, had dressed a number of his noblemen in the royal attire. Three of these imposters met their fates at the blade of Archibald. Eventually he was captured and mercifully released by the victor. Hotspur was killed.

In France, he displayed great courgae in battle against the English and was made Lieutenant-General of the Kings forces by Charles VII. His service to the French Crown earned him the Dukedom of Touraine in 1424.

He was killed in France at the Battle of Verneuil four months later.

3rd version

Archibald the Grim was succeeded by his eldest son,ARCHIBALD, 4TH EARL OF DOUGLAS, ist duke of Touraine, lord of Galloway and Annandale (1372-1424), who married in 1390 Lady Margaret Stewart, eldest daughter of John, earl of Carrick, afterwards King Robert III. In 1400 March and Hotspur Percy had laid waste eastern Scotland as far as Lothian when they were defeated by Douglas (then master of Douglas) near Preston. With the regent, Robert, duke of Albany, he was suspected of complicity in the murder (March 1402) of David, duke of Rothesay, who was in their custody at Falkland Castle, but both were officially declared guiltless by the parliament. In that year Douglas raided England and was taken prisoner at Homildon Hill by the Percys. He fought on the side of his captors at Shrewsbury (1403), and was taken prisoner by the English king Henry IV. He became reconciled during his captivity with the earl of March,whose lands had been conferred on Douglas, but were now, with the exception of Annandale, restored. He returned to Scotland in 1409, but was in constant communication with the English court for the release of the captive king James I. In 1412 he had visited Paris, when he entered into a personal alliance with John the Fearless, duke of Burgundy, and in 1423 he commanded a contingent of 10,000 Scots sent to the help of Charles VII. against the English. He was made lieutenant-general in the French army, and received the peerage-duchy of Touraine with remainder to his heirs-male. The new duke was defeated and slain at Verneuil (1424) with his second son, James; his persistent ill-luck earned him the title of the Tyneman (the loser).

Source: http://21.1911encyclopedia.org/D/DO/DOUGLAS_SIR_CHARLES.htm 

Father: Archibald Douglas, 3rd Earl of Douglas. 

1. Elizabeth Douglas b: ABT. 1394, Died: Bef 1451 
   Married     (1): John Stewart, EARL OF BUCHAN 
                    (2): William Sinclair,   Earl of Orkney 
                    (3): Sir Thomas Stewart 
2. Archibald "of Touraine" Douglas, Born: Abt 1390 Of, Douglas, Lanarkshire. Died: 26 Jun 1438 Restalrig Married: Euphemia Graham, Countess of Douglas
3. James Douglas, Earl of Abercorn,  Born: Abt 1392 Of, Douglas, Lanarkshire, Scotland Died: 17 Aug 1424 Battle Of Vernoil, Maine-Et-Loire, France Bur.: 24 Aug 1424 Tours Cathedral, Tours, Indre-Et-Loire, France Married: Beatrice
4. Margaret Douglas, Born: [1394], Scotland Married: William Earl Of Orkney
5. Helen Douglas,  Born: [1396], Scotland Married: Alexander Lauder
6. Mary Douglas, Born: [1398], Scotland Married: Sir John Glendoning

Further details on this entry would be welcome.