How to Bet the 2019 Kentucky Oaks/Kentucky Derby Double

Do you think you’ve identified the most likely winners of the 2019 Kentucky Oaks (G1) and Kentucky Derby (G1) at Churchill Downs? Then why don’t you combine your opinions and play the popular Oaks/Derby Double?

This specialty bet pairs the May 3 Kentucky Oaks with the May 4 Kentucky Derby in a classic “daily double” and attracts a few million dollars in wagers each year. If you can pick the winners of both races, the payoff can be enticing. Even the chalky double in 2018 that paired top contenders Monomoy Girl (Oaks) and Justify (Derby) returned 15-1.

But with large fields in both races, it can be easy to spread too deep in one or both races and significantly reduce your return on investment. A $1 ticket using two horses in both the Derby and the Oaks costs $4, using three horses in each race boosts the price to $9 and four apiece bumps the investment to $16. It might be worthwhile if you can catch a longshot in one (or both) races, but if you’re going to spread deep, it helps to play combinations involving favorites for larger base amounts to double, triple or quadruple the eventual payoffs.

As I mentioned in my preview of the Kentucky Oaks, I’m not convinced the 2-1 morning line favorite #4 Bellafina is unbeatable, and since she’ll be a short price in the wagering, I’ll take a stand and exclude her from my Oaks/Derby Double.

My top choice #5 Flor de La Mar (20-1) is one I’ll include, but since I’m trying to beat the favorite (and will nab a nice return on investment if successful), I’ll use several others too, emphasizing fillies who have won in the mud or shown the ability to race off the pace. #1 Out for a Spin (15-1), #3 Lady Apple (20-1), #7 Jaywalk (8-1), #12 Street Band (15-1) and #14 Restless Rider (6-1) all fit the bill.

In the Derby, I’ll include my top choices #7 Maximum Security (8-1) and #16 Game Winner (9-2), but I’ll also throw in a small ticket with #3 By My Standards (15-1), an improving colt who could be poised for a ground-saving trip after a break from post 3.

I’ll spend $36 on Oaks/Derby Double tickets, which is a bit more than I would usually consider. But if Bellafina comes up short and we catch a longshot winner in the Oaks, we’ll have a chance to catch a lucrative payoff on Derby Day.

$3 Double: 5,7,14 with 7,16 ($18) $2 Double: 1,3,12 with 7,16 ($12) $1 Double: 1,3,5,7,12,14 with 3 ($6)

Total: $36

Good luck!