These Kentucky Derby Winners Raced At Suffolk Downs In 1942 & 2004

Written By Dan Holmes on May 4, 2023
2 Kentucky Derby winners have raced at Suffolk Downs, from

All eyes will be on Churchill Downs in Louisville this Saturday for the Kentucky Derby. That famous track has been the site of many memorable horse racing moments.

Massachusetts has a piece of real estate with great horse racing heritage too: Suffolk Downs in East Boston.

While Suffolk Downs doesn’t host thoroughbred racing any longer, Massachusetts horse racing fans can celebrate the Derby there this weekend for a simulcast of the Run for the Roses.

Opened in 1935, Suffolk Downs felt the thundering hooves of many of the greatest horses in American racing history, including two who captured Kentucky Derby in Louisville.

Kentucky Derby winners who raced at Suffolk Downs


This Louisville-bred horse won the Kentucky Derby and Triple Crown in 1941, and captured the Massachusetts Handicap at Suffolk Downs in 1942.

Funny Cide

At the 2004 Massachusetts Handicap, or MassCap, 4-year old Funny Cide finished second by a head at Suffolk Downs. But the disappointment was hardly crushing. The prior season, Funny Cide won both the Derby and the Preakness Stakes.

The New York horse (first bred in that state to win the Kentucky Derby) finished third in the Belmont Stakes in 2003, missing out on the Triple Crown.

Kentucky Derby winners who have raced at Suffolk Downs, from
Funny Cide takes a turn with practice rider Robin Smullen during the early moring workout at Lone Star Park in Grand Prairie, Texas, Friday, Oct. 29, 2004, in preparation for the Breeders’ Cup Classic Saturday. (AP Photo/LM Otero)


Cigar did not win the Kentucky Derby, but of the great race horses, Cigar seemed to love racing in Massachusetts the most. Twice, in 1995 and 1996, Cigar won the Massachusetts Handicap, the last time as a 6-year old. Those two victories in East Boston were part of a 16-race winning streak for the winner of the 1995 Breeders’ Cup Classic.

Cigar, whose damsire was 1977 Triple Crown winner Seattle Slew, was foaled in Maryland. He was named American Horse of the Year in both 1995 and 1996, and retired to stud as the leading money earner in horse racing history.

Skip Away

Following the success of Cigar, the Florida horse Skip Away emerged as a dominant winner in East Boston. In 1997 and 1998, Skip Away won the Massachusetts Handicap, setting a race record in 1998 of 1:47:27 for 1 1/4 miles. That record was never broken.

Unfortunately for Skip Away, while he captured close to $10 million in purses in his career, he finished a disappointing 12th in the 1996 Kentucky Derby.

Suffolk Downs: Showcase for Kentucky Derby champions

Though only one horse has won both the Derby and Massachusetts Handicap, which was run from 1935 to 2008, the Suffolk Downs track welcomed many Derby winners.

Since it was typically run in the late summer, the MassCap hosted many horses over the years who had won or performed well in May at Churchill Downs. Notable horses include Alydar, who finished second in all three Triple Crown races in 1978, and Personal Ensign, a mare that won the 1988 Breeders’ Cup, but never was able to win at Louisville.

READ MORE: Basic Tips For Beginners Trying Their Hand At Kentucky Derby Betting

Seabiscuit at Suffolk Downs

The most famous horse to run at Suffolk Downs is arguably the most well-known in the sport: Seabiscuit, whose amazing career included an iconic match-race win over a Triple Crown winner.

Because Seabiscuit was a West Coast horse, he rarely traveled east to face the top horses in that part of the country. At only 15 hands tall, the horse was puny, and considered a runt. But during the Great Depression, Seabiscuit became a symbol of perseverance in America. In 1936, in a season where the little horse won five races, history was changed at Suffolk Downs in one of Seabiscuit’s rare appearances outside California.

Trainer Tom Smith saw Seabiscuit on June 29, 1936, at Suffolk Downs, as the horse was going through a training run. Smith urged Charles Howard to buy the horse and set himself up as trainer for Seabiscuit. Over the next several months, Smith used his unusual training methods to whip the horse into shape.

RELATED: Kentucky Derby Watch Parties At Massachusetts Casinos, Racetracks

By the next August in 1937, Seabiscuit was entered into the MassCap, and listed at 5-to-2 odds. On the afternoon of Aug. 7, Smith and Howard watched Seabiscuit cruise around the track to win his ninth consecutive race and set a Massachusetts Handicap record for 9 furlongs.

Seabiscuit at Suffolk Downs, from
Seabiscuit (3), with jockey Johnny “Red” Pollard, crosses the finish line to win the $50,000 Massachusetts Handicap at Suffolk Downs, Boston, Ma., Aug. 7, 1937. Seabiscuit set a new track record of 1:49 for the mile and an eighth. (AP Photo)

The following year, 5-year old Seabiscuit met defending Triple Crown champion War Admiral in a match race at at Pimlico Race Course in New York. In what was called “The Match of the Century”, Seabiscuit defeated the favored War Admiral, who was priced at 1-to-4.

The victory was heard by millions across the country via radio and cemented Seabiscuit’s place as a legendary horse.

Seabiscuit was named American Horse of the Year for 1938. In 1939 as part of a national tour, he appeared in Massachusetts one last time at Suffolk Downs.

Photo by AP Photo/JMH
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Dan Holmes

Dan Holmes is a Staff Writer for PlayMA with plenty of experience under his belt. Dan has written three books about sports and previously worked for the National Baseball Hall of Fame and Major League Baseball. He also has extensive experience covering the launch of sports betting in other states, including Ohio and Maryland. Currently, Dan is residing in Michigan with his family.

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