As fans of horse racing betting are well aware, from 2013-2018 favorites ruled at the Kentucky Derby with six straight chalk winners. However, long shots have a long, rich history at the Run for the Roses. Let’s take a look back at the seven biggest Kentucky Derby betting long shots to ever cash at the first jewel of the Triple Crown.

1. Donerail 91/1

Year: 1913

Return on $2 bet: $184.90

Recap: The biggest long shot to ever win the Kentucky Derby was Donerail, who cashed at 91/1. A number of horses held the led throughout the race, but it was Ten Point, the favorite, who was in front at the final turn.

Donerail tracked him down and ended up winning by a half-length. At the time, Donerail had set a track record time at Churchill Downs at 2:04 4/5.

Donerail would go on to win nine other times in his career, placing 11 times and showing 10. His career earnings amounted to $15,156, which translates to nearly $370,000 today. The purse for the 2019 Kentucky Derby is $3 million.

2. Country Home (65/1)

Year: 2019

Return on $2 bet: $132.40

Recap: The 145th Kentucky Derby go down as one of the most bizarre of all-time. Maximum Security, the pre-race favorite, ran well and ended up crossing the finish line first. However, for the first time ever in a Kentucky Derby, the horse who finished first did not win.

Maximum Security strayed well out of his running line as the horses made the final turn at Churchill Downs and impeded War of Will, the horse who was behind him. As they nearly tangled legs, it caused a bit of a traffic jam behind Maximum Security before he straightened out and ended up winning by 1¾ lengths. However, after the race, two competing jockeys filed a protest, the stewards took a long look at the replays and ended up disqualifying Maximum Security.

That led to Country Home – a horse very few bettors or experts considered before the race – becoming the winner of the 2019 Kentucky Derby at 65/1. That makes him the second-biggest long shot to ever win the Run for the Roses.

3. Mine That Bird 50/1

Year: 2009

Return on $2 bet: $103.20

Recap: Mine That Bird is a famous closer that paid in spades in 2009. Trailing for nearly most of the race -- the gelding was more than 12 lengths back at one point –he looked like he was shot out of a canon down the final stretch. Mine That Bird ended up winning by a whopping 6 3/4 lengths, dusting the field as a 50/1 longshot.

He would never win another race, although he did place second in The Preakness and third in the Belmont Stakes that year.

4. Giacomo 50/1

Year: 2005

Return on $2 bet: $102.60

Recap: The 2005 Kentucky Derby was a crowded race as there were 20 entries in the field. The iconic New York Yankees owner, George Steinbrenner, had a colt in the field, Bellamy Road, who was the morning-line favorite. However, it was Giacomo that came out of nowhere to surprise the crowd at Churchill Downs.

Giacomo, named for musician Sting’s son, was one of five horses who went off at 50/1 but was the one that ended up cashing. That proved to be jockey Mike E. Smith’s first win in the Run for the Roses, although he added a second in 2018 with Justify.

5. Gallahadion 36/1

Year: 1940

Return on $2 bet: $72.40

Recap: The 66th running of the Kentucky Derby took place in May 1940, just as the World War II was escalating in Europe. It was Bimelech who was expected to win as he was the shortest-priced favorite in Kentucky Derby history at the time with odds of 2-5.

However, Gallahadion ended up edging him by 1 ½ lengths to earn the win just as trainer Roy Waldron had been predicting all week. Gallahadion was owned by Ethel V. Mars, who was the widow of the owner of the famous candy-bar empire.

6. Apollo 33/1

Year: 1882

Recap: For many years, Apollo was the only horse to have broken one of the unspoken rules of the Kentucky Derby: never race in the Kentucky Derby without having raced as a two-year-old. That’s part of why his odds were so long to begin with. Justify (2018) became the second horse ever to win the Kentucky Derby without racing as a two-year-old.

In the 1882 Derby, it was 4-5 favorite Runnymede that had a healthy lead down the stretch. Many expected him to win but he faded slightly while Apollo closed with an epic burst, winning by a half-length.

At the time, this was just the eighth edition of the Run for the Roses. Apollo received a purse of $4,560 at the time while second place Runnymede earned $200.

7. Charismatic 31/1

Year: 1999

Return on $2 bet: $64.60

Recap: Charismatic was a complete afterthought at the 1999 Kentucky Derby. Early in his career, he was basically an overweight vagabond, entering in claiming races. He had lost seven straight prior to winning the Lexington Stakes two weeks before the Kentucky Derby.

At the Run for the Roses, he stunned everyone, upsetting favorite Excellent Meeting, which was one of three of Bob Baffert’s entries that was sure to win the race. Charismatic ended up winning by a neck.

He proved to be no fluke, though, as he went on to win the Preakness and placed third at the Belmont.