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In the bare knuckle boxing of the 1800s, the guard had an extended lead arm with the arms held relatively low, with the knuckles facing downward, and the legs very straight, which was effective under the London Prize Ring Rules, which replaced the Broughton rules in 1838. Under the rules, some actions were illegal, such as butting, hitting a downed man, hitting below the belt, gouging, biting, kicking opponent's knees, and grabbing below the waist. A round in match ended whenever a person hit the canvas so rounds could be long and fights often went over 50 rounds. Various throws, such as the cross-buttock and back heel, were used with in close. The extended guard worked well under these rules and with the longer range the fighters used. Under the Broughton Rules, the hands of the guard were held a little higher than under the later London Prize Ring Rules and the legs had more spring in them.

Little is known about the guard used by fighters and fighting rules before the great English pugilist Jack Broughton, a student of James Figg, devised the Broughton Rules in 1743. Broughton also invented "mufflers" (padded gloves), which were used in training and exhibitions. Under the Broughton Rules. not much was considered illegal when compared to the London Prize Ring Rules so a higher guard and quicker stance was necessary. There were no limitations against butting, gouging, kicking, or hitting below the belt. The rules mostly just kept a boxing match from becoming a wrestling match.

Gentleman John Jackson's Boxing Academy in 1821

Until the use of gloves became common, pugilists struck mostly with a vertical fist because it was considered less injurious to the fist to hit with a vertical fist than a horizontal one, especially when using hooks or swinging punches. However, they used a horizontal fist when the target warranted it, such as to the side of the neck. The vertical fist was thought to have a greater range, but, in fact, the arm's reach does not get longer just because the fist is rotated 90 degrees, unless you make some other body adjustment.

Due to the confrontations American soldiers had with Filipino natives in the Philippines during the Spanish-American War in 1898, the guard was raised from the low knuckles downward position to the higher knuckles forward position. When engaged in hand-to-hand combat, the Filipinos would slash the wrists of the extended arms of the American soldiers.

The wearing of gloves in a boxing match is a fairly modern innovation. Prior to 1866, when the Marquis of Queensbury Rules made the wearing of gloves mandatory, boxers fought bare-knuckled. Gloves, or “mufflers” as they were called, were used only in sparring. One may think that fighting bare-knuckled, would cause significant damage to the fist. A common injury among modern boxers is the “boxer’s fracture,” in which the outer two knuckles, and sometimes the outer metacarpals of the hand are broken from the impact of an unprotected punch. Many boxing greats have broken their fists in this way when engaging in street fights.

However, the risk is significantly reduced through the biomechanics of throwing a bare-fisted punch. Old style pugilism, which was built primarily on linear action, and emulated the thrust of a sword used a vertical fist, rather than today’s horizontal fist.

With a vertical fist, the entire arm is extended in one line from the shoulder through to the fist. The elbow is tucked beneath the arm as opposed to jutting outward, and the wrist is kept straight. This changes the angle at which the fist connects, and maximizes the striking surface by using the whole fist and not just the first two knuckles. Even when throwing a “rounding blow,” which is the ancestor of today’s hook, the vertical fist was used – either normally or inverted. Punching with a vertical fist provides fewer places in the arm for energy to “get lost” (like a bent elbow or wrist), and it provides more protection for the arm as a whole. The result is that that more kinetic energy is realized as force, and is distributed evenly across the fist. This protects the hand more than if the force was concentrated in one area, while still providing a powerful blow.

Professor Mike Donovan, an ex-middleweight champion, in his 1893 book The Science of Boxing, advocated using using a three-knuckle landing, vertical punch. Jack Dempsey was an advocate of the three-knuckle, vertical punch, as it worked well with his "power line" theory (similar to the Wing-chun centerline theory).

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