[2] Clifford entered on his military career when hardly more than twelve, being armed at the time of Jacob van Artevelde's death on 17 July 1345.
[3] In August 1350 he was engaged in the sea fight with the Spaniards near Winchelsea; and in 1355 he accompanied his father-in-law, Thomas de Beauchamp, 11th Earl of Warwick, on the expedition to Gascony.
In July 1370 he was appointed one of the wardens of the west marches; but according to Sir H. Nicolas, he is found defending the northern borders fourteen years earlier.
In 1377 he was made High Sheriff of Cumberland and governor of Carlisle, a city whose walls he appears to have inspected and found weak in the preceding year.
In August 1374 he was appointed one of the commissioners to settle the dispute between Henry de Percy and William, Earl of Douglas, relative to the possession of Jedworth Forest.
Roger de Clifford died 13 July 1389, being then possessed of enormous estates, chiefly situated in Yorkshire, Northumberland, Cumberland, and Westmoreland, but spread over several other counties.