[4] Matthews was born and raised in the lower East side of New York City in the Brooklyn area, near Corlear's Hook, on July 18, 1873, and excelled at baseball as a childhood sport, particularly pitching.

Boxing referee Charley White may have acted as his earliest manager and arranged his first bout with local boxer Johnny Bennis, who he knocked out in telling fashion.

[8] On October 29, 1896, Matthews knocked out English born boxer Stanton Abbott in the seventh of fifteen rounds at the Empire Athletic Club, in Buffalo, New York before a crowd of around 2,000.

[11] On December 21, 1897, Matthews won a twenty-round points decision against Mike Leonard at the Rienzi Athletic Club in Rochester, New York.

[2] On December 10, 1898, Ziegler fought a tame twenty-round draw with Matthews at the Queen's City Athletic Club in Toronto, Canada.

On August 25, 1898, he made his first unsuccessful attempt at the World Welterweight Championship against Mysterious Billy Smith at New York's Lenox Athletic Club, losing in a twenty-five round points decision.

[15] On September 14, 1899, Matthews defeated Bobby Dobbs in a twenty-fifth round disqualification at the Coney Island Athletic Club in Brooklyn, New York.

On December 2, 1899, Matthews defeated another exceptional Black boxer, welterweight Hugh McWinters, in a twenty-round decision at the Pelican Club in Brooklyn.

[2] On April 17, 1900 he took the World Welterweight Championship from Mysterious Billy Smith at the Broadway Athletic Club in New York, knocking him out only twenty eight seconds into the 19th round, before a crowd of 4,000.

[16] Smith was a 4 to 1 favorite in the early betting but may have lost some stamina from having to lose a pound prior to the bout to make the required weight of 142.

[2] On April 9, 1900, Matthews defeated New Jersey boxer Dan McConnell in a third-round technical knockout at the Niles Athletic Club in Youngstown, Ohio.

[21] One the same night according to several sources, Matthews defeated Billy Payne at the Niles Athletic Club in Youngstown, Ohio, in a fifteen-round points decision.

On May 4, 1900, he fought a ten-round draw with Kid Parker in Denver, Colorado which a few sources reported as a World Welterweight Title match.

[22] Matthews lost the world welterweight championship in a twenty-five round points decision on June 5, 1900 against contender Eddie Connolly at the Seaside Athletic Club in Brooklyn, New York.

[25] Matthews regained the World Welterweight Title from Rube Ferns on October 16, 1900, at the Cadillac Athletic Club in Detroit, Michigan, in a fifteen-round points decision.

[2][26] Matthews lost the 142 pound Welterweight Title to Ferns on May 24, 1901 before a crowd of 3000 in a tenth-round knockout at the Mutual Street Rink in Ontario, Canada.

Matthews had previously beaten Strauss on January 8, 1900, in a round twelve Technical Knockout at the Hercules Athletic Club in Brooklyn.

[28][29] By the final round of the January bout, Strauss was so exhausted his knees may have buckled as many as four times, and at a few points in the match he was fatigued enough that he slipped to the mat avoiding the blows of Matthews.

[30] On March 16, 1906, near the end of his boxing career, Matthews was knocked out by Rube Ferns in the ninth round at the International Athletic Club in Buffalo, New York.

According to the Boston Globe, on August 19, 1908, Matthew's last bout was likely a six-round newspaper decision against Patsy Sweeney at Ulmer Park, in Brooklyn, New York.

[2] In his early career, he worked briefly as a sparring partner for friend and great British born welter and middleweight boxer Tommy West, who ran a boxing school in Brooklyn.