Moving on to the United States, Fitzsimmons fought four more times in 1890, winning three and drawing one. Then, on 14 January 1891, in New Orleans, he won his first world title from Jack (Nonpareil) Dempsey. Fitzsimmons knocked out Dempsey (from whom the later Jack Dempsey took his name) in the 13th round to become the World Middleweight Champion. Fitzsimmons knocked Dempsey down at least 13 times and by the finish left him in such a pitiable condition that he begged him to quit. Since Dempsey would not do so, Fitzsimmons knocked him out and then carried him to his corner. On 22 July, police broke off his fight with Jim Hall after he had knocked Hall down several times. Fitzsimmons spent the next two years fighting non-title bouts and exhibitions until giving Hall a chance at the title in 1893. He retained the crown by a knockout in round four. He spent the rest of that year doing exhibitions, and on 2 June, he had scheduled a two-way exhibition where he would demonstrate in public how to hit the boxing bag and then how to box against a real opponent. Reportedly, two freak accidents happened that day: Fitzsimmons hit the bag so hard that it broke, and then his opponent of that day allegedly slipped, getting hit in the head and the boxing exhibition was cancelled. At a public sparring performance on 16 November 1894 at Jacob's Opera House, Syracuse, New York, Fitzsimmons knocked out sparring partner Con Riordan, who was carried off unconscious and died several hours later. Two months later Fitzsimmons was charged with manslaughter but was acquitted.

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Fitzsimmons knocked out sparring partner Con Riordan, who was carried off unconscious and died several hours later.