[1] Ryan fought only ten major bouts, but as many as twenty-five exhibitions including many Sullivan in his late career.

[3] After opening a Troy saloon in 1874, he caught the attention of the athletic director of Rensselaer Polytechnic Institute, Jim Killoran.

[1] Former heavyweight champion Jem Mace had been inactive for many years, and was believed to have vacated the title, making it open for contention.

On their arrival to the working capital of Pennsylvania, the Mayor of Pittsburgh made it clear to both parties that the illegal fight would not take place in his city, so the combatants moved to a more remote spot in West Virginia.

[4][5] In the most significant win of his career, Ryan defeated bare-knuckle heavyweight championship Joe Goss on 30 May 1880, in Collier's Station, West Virginia.

Ryan was nearly twenty pounds heavier and nearly six inches taller than Goss, a discrepancy which would have never been allowed in today's boxing, and may have made the difference in the match.

[1] John L. Sullivan and Ryan arrived in New Orleans on 6 February 1882, to determine who would hold the American heavyweight championship.

[10] Ryan was six years older, at least ten pounds lighter, but an inch or two taller, which gifted him with greater reach.

[10] Considered ancient for a modern boxer, the thirty-seven year old Ryan knew he was battered from his long career and admitted, "I meant to have retired before, but you know how it is.

[13][14] Sullivan's fame and his acceptance among both American aristocracy and the lower classes was unique and new in the boxing world, and would help both boxers draw large crowds to the exhibitions they would later stage in the Northeast.

Ryan was less active in boxing in 1883 when he knocked out Montana champion Jack Waite in a three-round exhibition on 21 October.

He continued to meet few opponents in 1884–1885, though on 19 January 1885, Ryan fought a no contest bout with Sullivan at New York's Madison Square Garden.

The referees split on a decision, so a draw was called, when a dozen police officers intervened and stopped the fight in the second round.

[17] The bout was fought on a boat in the rain using the London Prize Rules and close to 1,500 spectators had huddled nearby to see the match.

[1] The new Queensbury rules banned all forms of wrestling, which may have hurt Ryan in his next fight against the superior scientific boxer, Jack McCaulliffe.

On 13 November 1886, before a crowd of 8,000, Ryan had a non-title rematch with Sullivan, at the Mechanic's Pavilion in San Francisco, California; he lost by knockout in a 3-round contest.

He was down in the first from a short arm to the chin, though both boxers appeared to have traded some solid blows to the face before the round ended.

[23] Ryan performed in a series of lucrative and well-attended exhibitions with Sullivan, primarily in New England, from 1891 to 1897, before retiring from boxing.

[1] In their three-round exhibition in March 1896, in Visalia, California, 230 miles southeast of San Francisco, Sullivan was described as "beefy and far from looking like a pugilist, while Ryan was said to still be in good form.