The Biggest Breeders’ Cup Upsets, Race by Race (Part 1)

By Ray Wallin

The world of sports is full of upsets: David versus Goliath, the USA hockey team beating the Soviets in the 1980 Olympics, and my beloved New York Jets winning any game. If you have ever been at the track when a big longshot hits the feeling can be electric as someone has likely hit the bet of a lifetime. It is fun to root for the underdog.

While the Breeders’ Cup is like the All-Star Game of horse racing, the big favorites don’t always win. In fact, of 360 horses that have gone to post as the favorite, 112 have won, which is a win rate of 31%. This is a hair below how favorites normally perform. Of those favorites, 67 have gone off as odds-on which has resulted in 29 winners for a 43% win rate. Conversely, 45 horses have gone off at odds of 100-1 or worse and have produced only one winner.

So, what are the biggest upsets in each of the Breeders’ Cup races? We’ll give them to you from lowest to highest payout.

In Part 2, we will look at the remainder of the list. Which races do you think we’ll see a new biggest upset in this year?

16 Juvenile Turf Sprint

Bulletin ($10.60) – 2018

The Juvenile Turf Sprint is the new kid on the block having only been run three times since its inception in 2018. 2018 is also the year of the longest priced horse to win the race with Bulletin taking the field wire-to-wire at odds of 4-1. He would return for his sophomore campaign with an impressive win in the Palisades Turf Sprint at Keeneland, but has not won a race since and last raced at Randwick Race Course in Australia in May of 2021.

15 Juvenile Fillies Turf

Sharing ($29.60) – 2019

This chestnut filly took over the race late after pressing the pace the entire way to beat favorite Daahhey in the stretch as the pair past the tiring Sweet Melania. She would return for her sophomore campaign with a win in the Tepin Stakes at Churchill before shipping to Ascot where she finished second in the Grade 1 Coronation Stakes. She returned to the U.S. and won the Grade 2 Edgewood at Churchil but was retired before her 4-year-old campaign.

14 Juvenile Sprint

Hightail ($32.80) – 2012

This colt nipped the front-running 1-2 favorite at the wire to win by a nose in what would be his first and only career victory as the longest shot on the board in a five-horse field at 15-1. He would make one more career start two weeks later in the Grade 3 Delta Downs Jackpot Stakes finishing a lackluster fourth. This race was only contested twice, so Hightail has at least embedded himself in Breeders’ Cup history.

13 Sprint

Sheikh Albadou ($54.60) – 1991

This Grade 1 winner in Europe shocked the Americans by stalking and then running down pace-setter Media Plan and never looking back at 26-1. He would have a successful campaign the following year culminating with another trip to the States where he finished second to Rubiano in the Grade 1 Vosburgh at Belmont and ended his career with a fourth in the Breeders’ Cup Sprint, this time going off at 3-1.

12 Juvenile Turf

Fire at Will ($62.40) – 2020

This Mike Maker trainee ran down front-runner Outadore in the stretch and drew clear for a three-length lead over favorite Battleground to be the first of two horses to have record upsets in their divisions in 2020. Bettors gave him little respect off a front-running win in the Grade 2 Pilgrim Stakes in his previous start. After a disappointing eighth in the Grade 2 Fountain of Youth and a third in the Grade 3 Transylvania, he has been sidelined indefinitely.

11 Turf Sprint

Desert Code ($75.00) – 2008

In what was a thrilling finish that saw this colt bolt from 10th to first in the stretch would be the biggest race of his 24-race career at 36-1. He would return to defend his crown in 2009 still not getting any respect at the windows going off at 22-1. He finished 13th.

10 Dirt Mile

Dakota Phone ($77.40) – 2010

This gelding ran the race of his life at Churchill Downs going from last to first in dramatic fashion to win a photo against the speedy Morning Line. He would unsuccessfully go to post three more times, failing to hit the board in any of the races.

9 Marathon

Afleet Again ($85.20) – 2011

For a race that was contested six times, it provided some great moments, including Afleet Again’s big closing effort over the Churchill dirt at 41-1. He would only take the track once more after this upset, finishing fourth in the Grade 3 Valedictory at Woodbine.

Ray Wallin
Ray Wallin is a licensed civil engineer and part-time handicapper who has had a presence on the Web since 2000 for various sports and horse racing websites and through his personal blog. Introduced to the sport over the course of a misspent teenage summer at Monmouth Park by his Uncle Dutch, a professional gambler, he quickly fell in love with racing and has been handicapping for over 25 years.

Ray’s background in engineering, along with his meticulous nature and fascination with numbers, parlay into his ability to analyze data; keep records; notice emerging trends; and find new handicapping angles and figures. While specializing in thoroughbred racing, Ray also handicaps harness racing, Quarter Horse racing, baseball, football, hockey, and has been rumored to have calculated the speed and pace ratings on two squirrels running through his backyard.

Ray likes focusing on pace and angle plays while finding the middle ground between the art and science of handicapping. When he is not crunching numbers, Ray enjoys spending time with his family, cheering on his alma mater (Rutgers University), fishing, and playing golf.

Ray’s blog, which focuses on his quest to make it to the NHC Finals while trying to improve his handicapping abilities can be found at www.jerseycapper.blogspot.com Ray can also be found on Twitter (@rayw76) and can be reached via email at ray.wallin@live.com.