The Old Roger flag is a loose term for a historical variant of the pirate ensign Jolly Roger, whose motif consists of a skeleton on a black field, holding an hourglass in one hand and a dart striking a heart in the other. The general design is noted to have been used by a number of Golden Age pirates, but the association with the name Old Roger is modern.

The name "Old Roger" is an old humorous or familiar name for the devil, or death.

The design is described in several period accounts for several pirates, such as famous Golden Age pirates Edward Low, Charles Harris and Francis Spriggs.

The name "Old Roger" in association with the design is found in a news report in the Weekly Journal or British Gazetteer (London, Saturday, 19 October 1723; Issue LVII, p. 2, col. 1):

“Parts of the West-Indies. Rhode-Island, July 26. This Day, 26 of the Pirates taken by his Majesty Ship the Greyhound, Captain Solgard, were executed here. Some of them delivered what they had to say in writing, and most of them said something at the Place of Execution, advising all People, young ones especially, to take warning by their unhappy Fate, and to avoid the crimes that brought them to it. Their black flag, under which they had committed abundance of Pyracies and Murders, was affix'd to one Corner of the Gallows. It had in it the Portraiture of Death, with an Hour-Glass in one Hand, and a Dart in the other, striking into a Heart, and three Drops of Blood delineated as falling from it. This Flag they called Old Roger, and us'd to say, They would live and die under it.”

Edward Low's initial flag was described as a “Black Ensign [with] a white Skeleton in the middle of it, with a Dart in One Hand striking a bleeding Heart, and in the other an Hourglass”.

Francis Spriggs' flag was described in The Political state of Great Britain (Volume XXVIII, August 1724):

“..their black Ensign, in the Middle of which is a large white Skeleton, with a Dart in one Hand, and in the other an Hour Glass.”