The two ships opened fire just before 18:00 at a range of about , with "Shannon" scoring the first hit, striking "Chesapeake" on one of her forward gunports with two round shot and a bag of musket balls fired by William Mindham, the gun captain of the aftmost of "Shannon"'s starboard 18-pounders. "Chesapeake" was moving faster than "Shannon", and as she ranged down the side of the British ship, the destruction inflicted by the precise and methodical gunnery of the British crew moved aft with the American's forward gun crews suffering the heaviest losses. However, the American crew were well drilled and, despite their losses, returned fire briskly. As "Chesapeake" was heeling, many of their shots struck the water or waterline of "Shannon" causing little damage, but American carronade fire caused serious damage to "Shannon"s rigging. In particular, a 32-pound carronade ball struck the piled shot for the "Shannon"s 12-pounder gun that was stowed in the main chains; the shot was propelled through the timbers to scatter like hail across the gundeck.