The Run for the Roses, which is contested on the first Saturday in May at Churchill Downs on an annual basis, is the most popular horse race in North America. It features the top three-year-olds in training going against each other over a demanding distance of 1 1/4 miles on the dirt at the Louisville, Kentucky venue.

The outcome of the contest has varied dramatically over the previous 148 runnings, featuring everything from favorites coming out on top, to longshot winners as we witnessed in 2022 with Rich Strike, who went off at staggering 80-1 odds.

There is no exact formula for achieving success, but below are a few tips that can be helpful with your first Kentucky Derby wager.

1. Spread Your Money Around

My advice is to wager on multiple horses if you have a liking for more than one.

The Kentucky Derby is arguably the most daunting betting task that we have in our sport in North America. With 20 horses heading to the starting gate on most occasions, focusing on just a single contender will make your chore all the more difficult in hopes of making a score.

Nothing is stopping you from wagering on multiple entrants in the storied event, and with so many three-year-olds in the field, receiving a fair price on your selections is often the case.

2. Keep A Balance

My suggestion would be to utilize something in the range of 25-50 percent of your bankroll on show wagers.

In any particular race there is a bevy of different wagers that a bettor can make. The safest play, or the one with the best chance of receiving a return on your investment, is the show wager. Selecting a horse to finish either first, second, or third is still a challenging task when you have 20 thoroughbreds to choose from.

A show bet is the highest percentage play available. While it's not sexy and doesn't make for the best story to tell friends that you successfully collected on a show bet, I feel that it's a great way to get some money back following the Derby.

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3. Seek the Experts' Advice

There are numerous handicappers and journalists that have devoted a good portion of their lives to horse racing.

In particular, the staff affiliated with Churchill Downs are well-informed and intelligent, and they can help point you in a positive direction with selecting horses more often than not. While there are no guarantees with Kentucky Derby wagering, or any type of bet for that matter, seeking advice from people who have their fingers on the pulse of this fascinating sport is a wise move.

4. Take Some Chances, Keep it Fun

Cashing a ticket following the ‘Greatest Two Minutes in Sports’ will bring you a level of joy, a good story, and perhaps, a substantial windfall.

You can use your child’s birthday, grandma’s mailing address, a pin number, the flight number that got you to Louisville. Get creative with it! 

I’ve heard enough stories over the years of how people made a ‘Derby score’ that would surprise anyone, so have some fun!