This Friday, Ryan Garcia will take on Rolando “Rolly” Romero atop a bill that will take place in the heart of New York City, under the stars in Times Square. It is, to put it mildly, an atypical setup, the apparent advantage of outstanding real estate negated by the live crowd reportedly being restricted to a small audience of media and invitees. But whether you regard the setting as inspired or insipid, the card will ultimately stand or fall on the quality of the action inside the ropes.

Yet even if that action proves to be special, it will have to go some way to match the very best fights that have unfolded in the five boroughs over the decades.  

Trying to compile a list of the 10 most memorable or meaningful fights ever to take place in The City That Doesn’t Sleep is almost impossible – not because of the difficulty in finding that many but because of the challenge of reducing it to so few.

More even than Las Vegas, whose modern dominance of the sport is finally being challenged after an undisputed four-decade run, New York is a permanent fixture in boxing history. Were one so inclined, compiling a list of the top 50 New York fights would still require making some painful choices about what to include or exclude.

This list focuses exclusively on fights that wound up satisfactorily for all concerned (except the loser, naturally) and not those that were mired in scandal or negative notoriety – so there’s no Lennox Lewis-Evander Holyfield I, Riddick Bowe-Andrew Golota I or Emile Griffith-Benny Paret III. Roberto Duran’s stoppage of Davey Moore doesn’t quite make it; nor does Miguel Cotto’s revenge over Antonio Margarito, Felix Trinidad’s demolition of William Joppy or even the first war between Tony Zale and Rocky Graziano. Plenty of people might include them, and that’s fine; there are probably as many possible permutations for a list like this as there are people to make them.

But here, in chronological order, is one person’s list of 10 of the most significant nights in New York boxing history.

Jack Dempsey KO2 Luis Firpo

September 14, 1923

Polo Grounds

Plenty of people who aren’t even boxing fans are at least tangentially aware of this contest without even being aware that they’re aware, courtesy of George Bellows’ famous painting of Firpo knocking Dempsey through the ropes. That moment came after Dempsey had already put Firpo down seven times in the opening round, and would prove pivotal. Dempsey was helped back into the ring by fans and ringside media, and later acknowledged that without such help, he would never have made it back between the ropes. Dempsey survived and knocked out Firpo in the following round.

Joe Louis KO1 Max Schmeling

June 22, 1938

Yankee Stadium

Schmeling had upset the then-undefeated Louis two years earlier, knocking him out in the 12th round. A year later, Louis rebounded to win the heavyweight title, and one year after that he sought revenge against Germany’s Schmeling.

By this stage, the winds of war were beginning to blow, and Louis – only the second African-American to hold the crown – was supported passionately by White and Black alike against a man widely (and unjustly) perceived to be a representative of the Nazi regime. This time, Louis made no mistake, tearing into Schmeling and dispatching him inside a round, to the reported fury of Adolf Hitler.

Joe Louis KO13 Billy Conn 

June 18, 1941

Polo Grounds

The 18th(!) defense of Louis’ title reign would prove to be one of the most difficult, as Conn – who had surrendered the light heavyweight championship to step up in weight – outboxed him and built up a healthy lead on the scorecards going into the 12th. In that 12th round, Conn hurt Louis, prompting his fateful decision to try and knock Louis out in the 13th. In so doing, Conn left himself open to the bigger man’s punches, which put him down for the count with just two seconds remaining in the frame. In 1996, Ring Magazine dubbed this the sixth-greatest title fight of all time.

Rocky Marciano KO8 Joe Louis

October 26, 1951

Madison Square Garden

Louis had retired in 1948, but, saddled with debt, he was forced to return to the ring in 1950. After losing a challenge of Ezzard Charles for his old title, he ran up a string of eight wins before taking on the 37-0 rapidly rising contender Marciano. Although the veteran Louis started well, he soon fatigued, and from the sixth round onward the younger man was in the clear ascendancy. In the eighth, Louis was dropped by a left hook and then knocked clear out of the ring, prompting referee Rudy Goldstein to halt the contest without a count. The following year, Marciano became champion; Louis would not fight again.

Joey Maxim KO13 Sugar Ray Robinson

June 25, 1952

Yankee Stadium 

Robinson, the former welterweight and reigning middleweight champ, brought a record of 132-2-2 to his challenge of light heavyweight titleholder Maxim, and over the first 10 rounds he built a seemingly unassailable lead on the scorecards. But the 105-degree heat took its toll – first on referee Goldstein, who tapped out in the 10th round, to be replaced by Ray Miller; and then on Robinson, whose form began to desert him in the 11th and 12th and vanished for good in the 13th. At the end of that round, Robinson swung and missed with a wild right hand, falling flat on his face. He got up and kept swinging, but at round’s end he collapsed on his way to the stool, prompting a corner retirement. Back in the dressing room, Robinson’s handlers placed him in a cold shower as the disoriented fighter repeatedly shouted, “I’m not crazy!”

Floyd Patterson KO5 Ingemar Johansson

June 20, 1960

Polo Grounds

A year earlier, in a massive upset, Johansson knocked Patterson down seven times in the third round to snatch the heavyweight crown.

Twelve months later, Patterson boxed superbly, taking the fight to Johansson when appropriate and backing off when needed, before uncorking a right hand and trademark leaping left hook to drop Sweden’s Johansson in the fifth. A barrage of left hooks followed, culminating in one that dropped Johansson conclusively, making Patterson the first man to regain the heavyweight championship. (Also notable: It was the first title fight for referee Arthur Mercante.)

Joe Frazier W15 Muhammad Ali 

March 8, 1971

Madison Square Garden

What more needs to be said about this classic? Ali, banned from boxing at the height of his powers for refusing induction into the United States Armed Forces, had picked up two wins after three years out of the ring before challenging Frazier, who had become champ in his absence. The fight divided Americans along racial, political and social lines, and was a massive event, as typified by Burt Lancaster being on commentary and Frank Sinatra shooting photos from ringside for “Life” magazine. Frazier punctuated a winning performance with a final-round knockdown to etch his place in history and begin a three-fight rivalry that would consume both men.

Naseem Hamed KO4 Kevin Kelley 

December 19, 1997

Madison Square Garden

With a gaudy record of 28-0 (26 KOs), a flashy style and a confidence that didn’t so much border on arrogance as leave it in the dust, Hamed was already a popular and controversial fighter as he prepared to make his US debut.

Not until nine minutes after New York’s former titleholder Kelley had stepped between the ropes did Hamed complete his extravagant ringwalk, during which HBO’s Larry Merchant fought a losing battle against apoplexy. But it was an enraged Kelley who drew first blood, knocking down Hamed with a counter right hand at the end of the first.

Kelley forced Hamed to touch the canvas for an eight count in the second before Hamed scored his first knockdown of the night on a counter of his own. Halfway through the fourth, Hamed put Kelley down again, but then Kelley caused Hamed to touch his gloves to the canvas for a third knockdown, and finally Hamed dropped Kelley hard on a left hand, with Kelley unable to beat the count. It was a night that spoke both to Hamed’s potential and his vulnerabilities. The fire that burns brightest burns briefest, and within five years Hamed had retired.

Bernard Hopkins TKO12 Felix Trinidad

September 29, 2001

Madison Square Garden

Hopkins had already heightened tensions in the build-up to this fight for the undisputed middleweight championship by throwing the Puerto Rican flag to the ground and prompting a riot in San Juan’s Estadio Roberto Clemente.

Originally scheduled for September 15, the bout was postponed after the September 11 attacks, and the smell of fire and death was still in the air when the fighters finally met two weeks later. On an emotional night, with NYPD and NYFD members feted at ringside, Hopkins dominated the younger, favored Trinidad, dropping and ultimately stopping him in the final round.

Katie Taylor W10 Amanda Serrano

April 30, 2022

Madison Square Garden

In the first true women’s superbout, Ireland’s Taylor retained her undisputed lightweight title via split decision over Puerto Rico’s Serrano, despite seemingly being on the verge of stoppage defeat in the fifth. The nearly 20,000-strong crowd was deafening from start to finish, the action almost non-stop. The fight won the BWAA’s inaugural Female Fight of the Year award, with the two women sharing the honor again in their rematch two years later. They will return to the Garden for a third fight on July 11, 2025.

Kieran Mulvaney has written, broadcast and podcast about boxing for HBO, Showtime, ESPN and Reuters, among other outlets. He presently co-hosts the “Fighter Health Podcast” with Dr. Margaret Goodman. He also writes regularly for National Geographic, has written several books on the Arctic and Antarctic, and is at his happiest hanging out with wild polar bears. His website is www.kieranmulvaney.com.