Matthew Redman served in France and Spain under John of Gaunt 1st Duke Lancaster.

In 1370 Matthew Redman (age 42) was at the Court of the King of Portugal, probably on some diplomatic mission.

Froissart. Before 05 Aug 1388. As at that time the earl of Northumberland and the other lords and knights of that country knew nothing of their coming. When tidings came to Newcastle and to Durham that the Scots were abroad, and that they might well see by the fires and smoke abroad in the country, the earl (age 46) sent to Newcastle his two sons [Henry "Hotspur" Percy (age 24) and Ralph Percy (age 29)] and sent commandment to every man to draw to Newcastle, saying to his sons: 'Ye shall go to Newcastle and all the country shall assemble there, and I shall tarry at Alnwick, which is a passage that they must pass by. If we may enclose them, we shall speed well.' Sir Henry Percy (age 46) and sir Ralph (age 29) his brother obeyed their father's commandment and came thither with them of the country. The Scots rode burning and exiling the country, that the smoke thereof came to Newcastle. The Scots came to the gates of Durham and scrimmished there; but they tarried not long but returned, as they had ordained before to do, and that they found by the way took and destroyed it. Between Durham and Newcastle is but twelve leagues English and a good country: there was no town, without it were closed, but it was brent, and they repassed the river of Tyne where they had passed before, and then came before Newcastle and there rested. All the English knights and esquires of the country of York and bishopric of Durham were assembled at Newcastle, and thither came the seneschal of York, sir Ralph Lumley (age 28), sir Matthew Redman (age 60), captain of Berwick, sir Robert Ogle (age 36), sir Thomas Grey, sir Thomas Holton, sir John Felton, sir John Lilleburn, sir Thomas Abingdon, the baron of Hilton, sir John Coppledike and divers other, so that the town was so full of people that they wist not where to lodge.