[1] Sullivan fought New London featherweight Austin Rice a total of four times, with the first bout coming on September 15, 1896, in a ten-round draw in Queens, New York.

[3] On February 17, 1897, he knocked out Patsy Haley in front of a crowd of 2000, in the thirteenth round, at the New Polo Athletic Club in New York City.

[1][6] On March 4, 1898, he fought Patsy Broderick in what was billed as the 118 pound American title at the Waverly Athletic club in Yonkers, New York, before an impressive crowd of 2000, winning by technical knockout in the ninth round.

[7][8] On May 16, 1898, he defeated Sam Kelly in a twenty-round points decision by referee Jimmy Dime in front of a crowd of around three to four thousand at the Lenox Club in New York.

[10] Smith had the misfortune to break his left arm near the wrist in the second round, ending his chances to give a good showing in the match, and he was compelled to retire in the fifth.

[1][11] Less than two months later on November 11, 1898, he decisively lost the title to Black Canadian boxer George Dixon in a tenth round disqualification at New York City's Lenox Club.

[12] Beginning a slight decline, he was knocked out in the seventeenth round by Oscar Gardner on January 9, 1899 at New York's Lenox Athletic Club.

On rising, Gardner landed three solid blows to Sullivan's head, the last a wild left jab to the mouth that resulted in the knockout.

[15] On March 27, 1899, he would fight a twenty-five round draw with New York Jewish boxerJoe Bernstein, a three time contender for the World Featherweight Title.

"[17] After his defeat by Gardner, his best known, closest matched, and most frequent opponent would be Kid Broad, who he first met on November 28, 1899, losing in a twenty-round points decision in Brooklyn, New York.

[18] On February 22, 1902, after a three-month rest, he would lose to Terry McGovern, perhaps America's best known and most revered featherweight, in a fifteenth-round technical knockout in Louisville, Kentucky.

After the foul ended the fight, Sullivan looked as though he would rush Briggs and begin a more personal scuffle, though order was maintained.

[22] On February 29, 1904, in an important match, he lost to World Featherweight claimant Young Corbett II, in an eleventh-round TKO at the Mechanic's Pavilion in San Francisco.

[23] At least one source noted that Sullivan lost the match badly, describing him as "going to the floor again and again beneath under the hailstorm of blows that reached him from all sides."

Considering the fight one sided, one reporter wrote, "At no period of the battle was the issue in doubt, although in some of the earlier rounds Sullivan rallied fiercely and appeared for a few moments to be holding his own."

"[24] Summing up the outcome of the match, one reporter wrote, "Corbett left the ring without a mark, while on the other hand, Sullivan received a terrific beating.