Connolly never seemed in danger of a knockdown and had McPartland at a safe distance. In 1902, McPartland would contend unsuccessfully for the Lightweight Championship of the World against the great Joe Gans. On May 15, 1900, he defeated Perry Queenan in a six-round points decision at Tattersall's in Chicago, Illinois. Connolly took the initiative in most of the fighting. Queenan performed better in the fifth and sixth rounds, and appeared to have finished stronger, but the bout was close. Only 1,000 spectators witnessed the bout, a bit of a disappointment. Connolly boxed most effectively in the clinches, and with the frequent clinching in the bout, it appeared both boxers were wary of each other. Connolly took the World Welterweight Championship in a twenty-five round points decision on June 5, 1900 against reigning champion Matty Matthews at the Seaside Athletic Club in Brooklyn, New York. It was their fourth meeting. Matthews was down for a count of nine in both the eleventh and eighteenth rounds, in a bout that was described as "the best bout of the four", with Connally winning decisively without ever being knocked to the mat. Matthews was also down shortly before the final bell from a strong right to the face. On August 13, 1900, he lost the World Welterweight Championship to Rube Ferns, before a crowd of 1800 at the Olympic Club in Buffalo in a fifteenth-round technical knockout of a planned twenty-five. In the final round, Connolly through up his hands after three light shots to the ribs, indicating he could not continue the bout, and his seconds threw in the towel. On January 6, 1902, Connolly lost to one of the greatest American light and welterweights in American history, the great champion Joe Gans, a black boxer of considerable skill and achievement. Connolly lost in a five-round disqualification at the Washington Sports Club in Philadelphia. One reporter noted that Connolly, "did nothing but hug and wrestle, adding variety to his performance in the third by deliberately trying to butt the Balitmorean (Gans). A head butt is a foul usually resulting in an immediate disqualification. Connolly headbutted Gans as many as three times. The reporter also noted that Connolly clinched frequently and "wrestled" rather than boxed, probably in attempt to protest himself from the fierce assaults of Gans. By the time the referee ended the bout in the fifth, Connolly had been "rendered practically helpless" by the powerful punching of Gans.