How to bet the Kentucky Oaks/Derby Pick 6 at Churchill Downs

Profile Picture: J. Keeler Johnson

April 29th, 2021

The Kentucky Derby (G1) and Kentucky Oaks (G1) aren’t the only Grade 1 races taking place at Churchill Downs this week. Four other top-level stakes will be contested Friday and Saturday, and fans of multi-race wagers can play them all through the $2 Oak/Derby Pick 6.

The two-day wager kicks off Friday at 3:03 p.m. ET. In 2019, the Oaks/Derby Pick 6 handled $479,561, so the potential exists for large payoffs if you can construct a winning ticket and beat some favorites.

Let’s take a race-by-race look at the sequence, then assemble a ticket on a $120 budget.

Leg 1: La Troienne S. (G1)

#2 Shedaresthedevil (8-5) showed an affinity for the Churchill Downs main track when she upset the 2020 Kentucky Oaks (G1).

The speedy Brad Cox trainee recently returned from a layoff to win the Azeri (G2) in gate-to-wire fashion, over next-out Apple Blossom H. (G1) winner Letruska, so any way you slice it, Shedaresthedevil is the filly to beat.

We’ll also include #5 Paris Lights (8-1), a determined winner of the Coaching Club American Oaks (G1) last summer.

The daughter of Curlin kicked off 2021 with a tenacious victory in the seven-furlong Distaff H. (G3) and can step forward in her stretch back out around two turns.

Leg 2: Kentucky Oaks (G1)

The stretch-running #10 Malathaat (5-2) is undefeated in four starts and finished fast to win the Ashland (G1) with an eye-catching late surge.

She’ll be tough to deny, as the only Grade 1 winner in the field, but we’ll also include #6 Travel Column (3-1), a versatile filly who dominated the Fair Grounds Oaks (G2) last month. Cox has won two of the last three editions of the Kentucky Oaks, and Travel Column is proven at Churchill Downs, where she rallied to win the Golden Rod (G2) last fall.

Leg 3: Derby City Distaff (G1)

We’ll single #4 Gamine (1-5), the champion female sprinter of 2020. She looms as the lone speed and kicked off 2021 with an easy victory in the Los Flores (G3) at Santa Anita earlier this month.

Leg 4: Churchill Downs S. (G1)

Eight-year-old #9 Whitmore (7-2) dominated the 2021 Breeders’ Cup Sprint (G1), but he has been beaten in both of his runs this year, and his 15-for-40 record indicates he might not be the type of horse to single in a Pick 6.

We’ll spread deep, with 2019 Hopeful (G1) winner #3 Basin (8-1), Commonwealth (G3) victor #4 Flagstaff (3-1), the Grade 1-placed #5 Tap It to Win (8-1), and recent allowance winner #7 Shashashakemeup (12-1).

Leg 5: Old Forester Bourbon Turf Classic (G1)

We’ll take a stand with Pegasus World Cup Turf (G1) winner #3 Colonel Liam (3-1), who boasts four wins from five starts on turf.

The consistent four-year-old recently unleashed a powerful stretch kick to overcome a slow pace and win the Muniz Memorial (G2), with a massive 119 Brisnet Late Pace rating.

Leg 6: Kentucky Derby (G1)

Our top choice in the “Run for the Roses” is #17 Highly Motivated (10-1), who appears primed for a peak performance, after he battled to a runner-up effort in the Blue Grass (G2). The Chad Brown trainee has only run twice this season and figures to get a perfect stalking trip.

We’ll include Florida Derby (G1) winner #1 Known Agenda (6-1) and Louisiana Derby (G2) victor #9 Hot Rod Charlie (8-1), though we’ll oppose morning-line favorite #14 Essential Quality (2-1).

The Blue Grass winner figures to wind up farther off the pace than usual and might not have the same upside as some of his rivals.

$2 Oaks/Derby Day Pick 6: 2,5 with 6,10 with 4 with 3,4,5,7,9 with 3 with 1,9,17 ($120)

Good luck!