What does the expression “a Roland for an Oliver” mean and Where does it come from?

The expression “a Roland for an Oliver” means: Tit for tat; a blow for a blow; an eye for an eye.

There was an actual Roland, a knight who fought under Charlemagne and who was killed in a rear-guard action in the Pyrenees in A.D. 778.

From his heroic action grew the famous medieval Chanson de Roland (Ballad of Roland) and other legends that spread into all parts of Europe.

In one popular form the story was of a most romantic friendship between Roland and one of his companions, Oliver, who was the equal of Roland in every respect.

They remind one of the Bobbsey twins: Whatever one could do, the other could do with precisely the same ability.

Eventually the two engaged in a combat which, though fought for five days, ended in a tie.

In some accounts, both were killed in the action in the Pyrenees, Roland by an accidental blow by his friend Oliver, who had himself received a fatal wound. Thus the two remained equal in death.

Because of the various monumental deeds accredited to the two heroes, the saying is also sometimes employed to mean one tall tale to match another.