On 9 April 1813 the U.S. Frigate Chesapeake returned to Boston after a cruise against British commercial shipping. Over the next several weeks she was refitted and received a new Commanding Officer, the recently promoted Captain James Lawrence. Many of her officers were replaced and a large percentage of her crew was newly enlisted. Though the ship was a good one, with a well-seasoned Captain, time would be necessary to work her men into a capable and disciplined combat team.

However, the time was not available. Blockading off Boston was HMS Shannon, commanded for the past seven years by Captain Philip Broke, whose attention to gunnery practice and other elements of combat readiness was extraordinary. Shannon and Chesapeake were of virtually identical strength, though the American ship's crew was rather larger, and a duel between the two was attractive to both captains. Broke even issued a formal challenge, though it did not reach Lawrence, whose previous experience with British warships had convinced him that they were not likely to be formidable opponents.

Chesapeake left Boston Harbor in the early afternoon of 1 June 1813. The two ships sailed several miles offshore, where Shannon slowed to await her opponent, who approached flying a special flag proclaiming "Free Trade and Sailors' Rights" in recognition of America's prewar grievances against British policies. Though Lawrence had a brief opportunity to rake, he did not do so, but closed to place his port broadside against Shannon's starboard battery. Somewhat before 6 PM the ships opened fire, both hitting, but the British guns did more damage and produced crippling casualties on Chesapeake's quarterdeck. Captain Lawrence was mortally wounded by small arms fire and had to be taken below, giving his final order "Don't give up the ship!"

The American ship was soon out of control. The two frigates came together. Captain Broke led his boarding party onto Chesapeake's quarterdeck, where they met fierce but disorganized resistance. Assisted by cannon and small arms fire from on board Shannon, they soon gained control above decks, though Captain Broke was badly wounded in the process. Some fifteen minutes after the battle began, Chesapeake was in British hands.

Casulaties were heavy: more than sixty killed on Chesapeake; about half that many on Shannon. The latter's cannon had made more than twice as many hits, and her boarding party demonstrated decisive superiority in hand-to-hand fighting. The action, which greatly boosted British morale, provided another of the War of 1812's many convincing examples of the vital importance of superior training and discipline in combat on sea and land.