Taking the Canadian Featherweight Championship

He began boxing professionally around 1894, taking the Canadian Featherweight Title at only eighteen on April 3, 1894, in five rounds in his hometown of Saint John, New Brunswick. He won the bout in a five-round points decision.^[1]

Connolly defeated Frank Garrard, a competent featherweight, on October 15, 1895, in a third-round knockout in Cleveland, Ohio. On January 10, 1896, he defeated Jimmy Dime at the Cleveland Athletic Club in Cleveland, Ohio, in a third-round knockout. These victories were instrumental in his quick rise in the boxing world.^[1] In January 1893, Dime had won the equivalent of the American Lightweight Championship at 130 pounds in Fonda, New York.^[2]

On August 13, 1896, fighting on his home turf of Saint John, New Brunswick, Connolly drew in six rounds with Stanton Abbott at the Mechanics Institute.^[1] The fighting was rather subdued and the crowd was small, however, as a New Brunswick magistrate, under pressure to curtail professional boxing, had threatened to arrest not only the principals in the fight but the spectators as well if a bout took place. The police chief and ten constables present at the bout apparently did not prevent the fight from taking place.^[3]

Taking the World Lightweight Championship of the British Empire

On November 24, 1896, Connolly took the British Empire World Lightweight Championship in Birminghamp, U.K. against English champion Tom Causer in a fifth-round knockout. It was an important win, and a widely recognized World Title, though not recognized worldwide, particularly the United States. Causer was a formidable opponent who according to one source, had lost only one bout prior to 1896.^[4] He was the favorite in the pre-fight betting at odds of 6 to 4 and a sizable purse of 200 pounds was at stake.^[5] The fighting was fierce and often close throughout, with the first full count in the fifth round.^[6]

Brutal bout with English boxer Dick Burge

On January 28, 1897, Connolly fought the great British boxer Dick Burge to a ten-round draw at the Olympic Club in Birmingham, England. Burge was the favorite at 143 pounds, with Connolly five pounds lighter at 138. The bout "caused unusual excitement, crowds flocking to the doors of the clubhouse, and it required extra policemen to preserve order." The sixth and seventh rounds were marked by particularly fierce fighting, with Burge connecting solidly to Connolly's face when he nearly slipped in the sixth, knocking him to the canvas for a count of nine, from which he quickly recovered.^[7] At least one source wrote that Burge had the edge in the fight and should have received the decision, despite having over a six-inch disadvantage in reach. The bout was stopped in the tenth round largely as a result of the fierceness of the fighting and the conditions of the competitors. Spectators, the manager of the Olympic Club, and several of the police voiced their desire to stop the fighting.^[8] Connolly's head and face were badly battered in the bout. According to Chicago's InterOcean, Burge, angered perhaps by the decision or confused by the fierceness of the contest, began fighting his own cornermen at the conclusion of the fight, and attempted to get at Connolly's trainer.^[9][10]

On March 28, 1897, Connolly met fringe world welterweight contender Paddy Fenton at the Suffolk Athletic Club in Boston, Massachusetts, losing in a fifteenth round disqualification. Connolly was disqualified for a punch to the groin of Fenton two minutes and thirty seconds into the fifteenth round.^[11] The victory for Fenton over a future Welterweight Champion, even if it was the result of a foul, may have been one of his most notable. Around September 1911, around the age of thirty-eight, Fenton would perform an exhibition bout with the young welterweight Abe "The Newsboy" Hollandersky, a future Panamanian Heavyweight Champion, at the New London County Fair.^[12]

Losing the World Welterweight Championship to Rube Ferns

Rube Ferns, Welterweight Champion

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.^[24]

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.^[25][1]

On April 18, 1902, he knocked out Barney Connors in four rounds at the Wabash Athletic Club in Chicago, Illinois. Connolly put Connors on the mat for the final count with a right swing to the jaw.^[26]

Facing English Middleweight Champion Jack Palmer

On July 19, and August 23, 1902, Connolly faced boxer Jack Palmer twice at the Ginetts Circus in New Castle, England, losing the first bout in a twenty-round decision, and the second in a sixth-round technical knockout.^[1] In their third and final meeting, on November 24, 1902, Connolly lost to Palmer in London at the National Sporting Club in a fifteen rounds points decision. Palmer was considered an English Middleweight Champion at the time of the bout. Palmer took $1000 for the win, with Connolly receiving only $250. The battling was hard and fast throughout. Fighting normally as a welterweight, Connolly may have been outweighed by the middleweight champion. At least three sources considered the bout for the Middleweight Championship of England at 158 pounds, though Connolly, perhaps because of his weight or his status as a resident of America was not eligible to box for the British title.^{[27][28][29][2][30]}

Unsuccessful attempt at the British Empire Welterweight Championship

On September 15, 1902, Connolly was defeated by English boxer Tom Woodley in an eleventh round points decision at the Wonderland Club in London. The bout was staged as a match for the British Commonwealth Welterweight Title at 144 pounds. Connolly had the lead until the sixth round when the tide turned and he was nearly knocked out by Woodley, and for the remaining five rounds, Woodley took control, finally winning on points.^[31] In a rematch on January 26, 1903, at the National Sporting Club in London, Connolly beat Woodley in a fifteen-round points decision.^[32]