Grapeshot was a kind of anti-personnel ammunition used in cannons. Instead of a solid shot, a mass of loosely packed metal balls in a canvas bag was loaded. On firing the balls spread out from the muzzle at high velocity, giving an effect similar to a shotgun but scaled up to cannon size.

Cannon would use solid shot to attack enemy artillery and troops at longer range, and switch to grape when they or nearby troops were charged. Battles in which grapeshot was famously and effectively used include

• Battle of Culloden, 1746, Jacobites under Bonnie Prince Charlie v Government forces under the Duke of Cumberland
• Borodino, 1812 (Prince Mikhail Kutuzov (Russia) v Napoleon Bonaparte (France) ).

Napoleon, when a brigadier general during the later stages of the French Revolution, famously dispersed a Royalist mob on the streets of Paris with a "whiff of grapeshot" on 5 October 1795. He was rewarded with the command of the Army of Italy in 1796, and his victories at the battles of Lodi, Castiglione , Arcola and Rivoli provided a springboard for his military and political ambitions.

Since the passing of breech loaded cannon, and the introduction of the fixed round, grape has been replaced by cannister or case round where a brass cartidge contains the shot.

The Shrapnel round was an invention to deliver the effect of grape shot at a distance.