In July 1975, she entered a highly anticipated match race with Kentucky Derby winner Foolish Pleasure, in which she broke down.

Janney, a cousin of prominent horseman Ogden Mills Phipps, later became the chairman of the Bessemer Trust.

[4] Ruffian made her debut at Belmont Park on May 22, 1974, in a 5+1⁄2-furlong maiden special weight race, going off at odds of 4–1 in a field of ten.

[6] On June 12, Ruffian faced stiffer company in the 5+1⁄2-furlong Fashion Stakes, including two other undefeated fillies, Copernica and Jan Verzel.

[7] Ruffian made her third start on July 10 at Aqueduct Racetrack in the Astoria Stakes over a distance of 5+1⁄2 furlongs.

Ruffian broke a step slow but soon took the early lead, setting a "brutally fast" pace of 0:213⁄5 for the first quarter and 0:441⁄5 for the half.

Ruffian responded by inching back into the lead, then finally drew away to win in a stakes record time of 1:09 for six furlongs.

Another trainer said that she could have won either division of that year's Hopeful Stakes, Saratoga's most prestigious race for colts, by twenty lengths.

[11] Ruffian was entered in the Frizette Stakes on September 26 but was scratched on the day of the race due to a high temperature.

Veterinarian James Prendergast detected a hairline fracture of her right hind ankle, ruling her out for the rest of the year.

When asked why he thought Ruffian had not shown any signs of being hurt until later, he replied, "She is a very tough filly, and doesn't like to show any weaknesses."

Turning into the stretch, she started to draw away and eventually won by 13+1⁄2 lengths while setting a new stakes record of 1:474⁄5 for nine furlongs.

[18][19] In the Coaching Club American Oaks on June 21 at Belmont Park, she was again made the 1-10 favorite despite racing for the first time at a distance of 1+1⁄2 miles.

Her connections had been asked about running her against colts since early in her career, and Whiteley thought that the Travers Stakes at Saratoga in August would be a good opportunity.

"[22] However, Janney felt obligated to enter in the July match race due to media and public expectations.

Vásquez chose to ride Ruffian in the match race, believing her to be the better of the horses; Braulio Baeza rode Foolish Pleasure.

The "Great Match" was heavily anticipated and attended by more than 50,000 spectators, with an estimated television audience of 20 million.

Little more than 1 furlong (201 m) later, Ruffian was in front by half a length when she changed leads, followed by a crack audible to both jockeys.

She went on running, pulverizing her sesamoids, ripping the skin of her fetlock and tearing her ligaments until her hoof was flopping uselessly.

[24] Ruffian was immediately attended to by a team of four veterinarians and an orthopedic surgeon, and underwent an emergency operation lasting twelve hours, during which she had to be revived twice after she stopped breathing.

[25] When the anesthesia wore off after the surgery, she thrashed about wildly on the floor of a padded recovery stall as if still running in the race.

"[4] At around 9 p.m. on July 7, 1975, after the day's races concluded at Belmont Park, Ruffian's remains were buried in a private ceremony in the infield.

[28] In August 2023 it was announced that Ruffian's remains were exhumed from her grave at Belmont Park and reinterred in Marchmont Cemetery at Claiborne Farm in Kentucky where she was born.

Janney expressed hope that more members of the public would be able to pay their respects to Ruffian in her new resting place.

As it is natural for horses to thrash and kick when coming out of anesthesia, a "recovery pool" was developed so that they awaken suspended in warm water and don't re-injure themselves.

[31] Ruffian's breeding may be considered at least partly to blame for her broken leg; her sire, Reviewer, suffered three breakdowns in his racing career.

[25][32][33] Shenanigans, Ruffian's dam, was euthanized following intestinal surgery on May 21, 1977, when she broke two legs while recovering from anesthetic.

To help prevent similar tragedies, the industry has directed research into improved early detection, surgical techniques and rehabilitation methods.

Sports Illustrated included her as the only non-human on their list of the top 100 female athletes of the century, ranking her 53rd.

[38] In the summer of 1975, folk singer Joan Baez dedicated a version of the song "Stewball" to Ruffian.