Captain Hull sailed on a cruise from Boston on August 21, just in time to dodge an order from Washington to remain in port until further orders.  On the afternoon of August 19, when several hundred miles to the eastward of Halifax, he sighted the British frigate Guerriere.  Her commander, Captain James E. Dacres, was an old acquaintance of Hull, and the two had made a wager of a hat during peace that if they ever met in battle the other would run.

The British officer was as anxious as Hull for a fight, and they drew near each other, both confident of winning the wager made half in jest a brief time before.

Great interest attaches to this naval battle, for it was the first of its kind and a fair test of the respective prowess of ships of and crews of that nature.  The Constitution was somewhat the superior, carrying 55 guns and four hundred and sixty-eight men, while the Guerriere had 49 guns and two hundred and sixty-three men, but all of the latter were under fine discipline, while most of the Americans were green hands.  Captain Dacres was confident of his superiority, and had no doubt that when the two frigates met the Constitution would be compelled speedily to strike her colors.  He waited for the American to come up, each having cleared for action.

A little after four o’clock the two exchanged broadsides, but they were so far apart that no damage was done.  Dacres manoeuvred for a raking position, but Hull would not permit it, nor could he obtain one for himself.  There was much wearing and manoeuvring, which prevented the firing on either side from being effective.  Each was wary of the other and took the utmost pains to prevent his securing any advantage.

When it became certain that the battle was to be one at close range, Hull ordered the firing to cease, in order that the fullest preparation could be made for the next broadside.  He knew the skill of his men in marksmanship, and determined to hold his fire until the most advantageous position was reached.  As he drew near his enemy, the latter continued firing, and some of her shots were so effective that the crews cheered.  The Americans, most of them barefooted and stripped to the waist, were standing beside their guns eager and impatient for the order to fire, but Hull, when appealed to, shook his head.  It was a proof of the fine discipline of the American crew that when they saw two of their comrades killed by the fire of the enemy, they silently waited without murmur for the order whose delay they could not comprehend.

Not until about a hundred feet distant and in the exact position desired did Captain Hull give the order to fire as the guns bore.  To quote Maclay:  “In an instant the frigate belched forth a storm of iron hail that carried death and destruction into the opposing ship.  The effect of this carefully aimed broadside at short range was terrific.  The splinters were seen to fly over the British frigate like a cloud, some of them reaching as high as the mizzen top, while the cheers of her men abruptly ceased and the shrieks and groans of the wounded were heard.  The Americans had struck their first earnest blow, and it was a staggering one.  The Englishman felt its full weight, and perhaps for the first time realized that this was no child’s play.”