In "Jeffries Versus Dempsey," Robert E. Howard imagines a fierce and evenly matched boxing bout between two legendary heavyweights, Jim Jeffries and Jack Dempsey, incorporating real-life boxing techniques and historic fighters' knockouts into the narrative. The fight is described in detailed rounds, showcasing the fighters' strategic maneuvers, powerful punches, and resilience.

The bout begins with both fighters cautiously engaging, with Dempsey initially taking the upper hand with his speed and aggression, landing a series of punches that stagger Jeffries. However, Jeffries quickly recovers, demonstrating his blocking skills and counterattacks. As the rounds progress, the match becomes more intense, with both fighters landing significant blows, showcasing their strength and determination. Despite Dempsey's speed and agility, Jeffries' powerful defense and strategic punches allow him to solve Dempsey's attack pattern.

In the pivotal fourth round, the fight reaches its climax. Both fighters exchange devastating punches, with Dempsey landing a series of blows that stagger Jeffries. However, Jeffries responds with his own powerful punches, ultimately knocking Dempsey down multiple times. The round ends dramatically with both fighters landing simultaneous punches that send them to the mat. Jeffries recovers quicker, ultimately winning the match by count-out as Dempsey fails to beat the ten-count despite his efforts to continue fighting.