The Road to the Breeders’ Cup: Win and You’re In and the Dirt Dozen

The countdown to the 2026 Breeders’ Cup World Championships is on, and this weekend is one of the biggest stops on the road to Keeneland.

The Breeders’ Cup runs at Keeneland on Friday, October 30 and Saturday, October 31. Fourteen Grade 1 Championship races bring together the best Thoroughbreds in North America and plenty of top raiders from around the world, with more than $34 million in purses and awards across the two days.

Before we get there, a big group of horses can still lock in a starting spot through the Breeders’ Cup Challenge Series, better known as Win and You’re In. The Breeders’ Cup Dirt Dozen runs alongside it and hands out valuable fee credits to horses heading for the Championships.

Below we break down how the two series differ, then walk through every Breeders’ Cup race that matters from Friday to Sunday.

What Is Breeders’ Cup Win and You’re In?

The Breeders’ Cup Challenge Series is the automatic qualifying series for the World Championships, and 2026 marks its 20th year. Designated races run throughout the season in North America and overseas, and each one links to a specific Championship race. This year the series features 95 qualifying races across 14 countries. Fifty of them take place in North America, and Breeders’ Cup has set aside a record $6.5 million in free entry fees.

When a horse nominated to the Breeders’ Cup wins one of these races, it earns an automatic starting spot in the matching Championship division. Breeders’ Cup also pays the pre entry and entry fees. The person who nominated the horse collects a $10,000 nominator award. Connections of a winner that is not yet nominated can still claim the rewards by nominating the horse before the October 19 pre entry deadline.

Travel support helps too. Every Championship starter based in North America but outside Kentucky receives a $10,000 travel award, and starters based outside North America receive $40,000.

The short version is simple. Win a designated Challenge race and the horse has a guaranteed place in the gate at Keeneland.

That makes this a massive weekend. Keeneland, Belmont Park and Santa Anita stage 15 Win and You’re In races between them from Friday to Sunday, and 10 of those 15 are for juveniles.

Win and You’re In Races This Weekend

Friday, October 2: Keeneland Opens Fall Stars Weekend

Keeneland opens its 90th Fall Meet on Friday, and the first afternoon of the 25th Fall Stars Weekend brings three Challenge races. First post is 1:00pm ET.

• The $650,000 Grade 1 Darley Alcibiades sends its winner to the Breeders’ Cup Juvenile Fillies. The juvenile fillies go 1 1/16 miles on dirt.

• The $400,000 Grade 2 Stoll Keenon Ogden Phoenix is a 6 furlong dirt sprint for 3 year olds and up. The winner books a spot in the Breeders’ Cup Sprint.

• The $400,000 Grade 2 Jessamine switches the juvenile fillies to turf over 1 1/16 miles, with a Breeders’ Cup Juvenile Fillies Turf berth on the line.

Saturday, October 3: Keeneland’s Five Stakes Card

Qualifying action continues on a huge Saturday in Lexington. Keeneland runs five stakes worth $3.5 million, and three of them carry Win and You’re In status. First post is again 1:00pm ET.

• The $1.25 million Grade 1 Coolmore Turf Mile is the richest race of the weekend, and its winner goes straight to the Breeders’ Cup Mile. The $650,000 Grade 1 Claiborne Breeders’ Futurity for 2 year olds over 1 1/16 miles on dirt feeds the Breeders’ Cup Juvenile. The $400,000 Grade 2 Thoroughbred Club of America for fillies and mares over 6 1/2 furlongs on dirt feeds the Breeders’ Cup Filly & Mare Sprint.

• The $800,000 Grade 1 First Lady and the $400,000 Grade 2 Woodford complete the card. Neither one is a Win and You’re In race this year, according to Keeneland’s own stakes announcement, which lists eight qualifiers across the weekend.

Saturday, October 3: Belmont Park Breeders’ Cup Preview Day

Belmont’s Breeders’ Cup Preview Day offers four more automatic qualifiers inside a six race graded stakes program worth $1.9 million. First post is 12:05pm ET, and the stakes run in this order on the NYRA race calendar.

• The $200,000 Grade 3 Matron kicks off the stakes action at 2:50pm. It is not a Challenge race.

• The $250,000 Grade 2 Miss Grillo follows at 3:22pm. The juvenile fillies go 1 1/16 miles on turf for a Breeders’ Cup Juvenile Fillies Turf berth.

• The $500,000 Grade 1 Champagne goes to post at 3:53pm for its 155th running. The one mile dirt test for 2 year olds hands its winner a free spot in the Breeders’ Cup Juvenile.

• The $500,000 Grade 1 Frizette runs at 4:31pm. It carries Breeders’ Cup value too, but through the Dirt Dozen rather than Win and You’re In. More on that below.

• The $200,000 Grade 3 Futurity over 6 furlongs on turf at 5:06pm offers a Breeders’ Cup Juvenile Turf Sprint berth.

• The $250,000 Grade 2 Pilgrim closes the 11 race card at 5:39pm. The juveniles go 1 1/16 miles on turf, and the winner heads for the Breeders’ Cup Juvenile Turf.

Saturday, October 3: Santa Anita Keeps the West Coast Busy

The road to the Breeders’ Cup runs through California as well, with three more Win and You’re In races at Santa Anita.

• The $300,000 Grade 1 American Pharoah for 2 year olds over 1 1/16 miles on dirt feeds the Breeders’ Cup Juvenile. That makes three Juvenile berths up for grabs on Saturday alone, with the Breeders’ Futurity and Champagne running earlier in the day.

• The $200,000 Grade 2 Oak Leaf for juvenile fillies over 1 1/16 miles on dirt feeds the Breeders’ Cup Juvenile Fillies. The $200,000 Grade 2 Rodeo Drive over 1 1/4 miles on turf sends its winner to the Breeders’ Cup Filly & Mare Turf.

Sunday, October 4: Keeneland Closes Fall Stars Weekend

Fall Stars Weekend wraps up with two more automatic qualifiers on a three stakes program. First post is 1:00pm ET.

• The $650,000 Grade 1 Juddmonte Spinster for fillies and mares over 1 1/8 miles on dirt feeds the Breeders’ Cup Distaff. The $400,000 Grade 2 Castle & Key Bourbon for 2 year olds over 1 1/16 miles on turf feeds the Breeders’ Cup Juvenile Turf.

• The $350,000 Grade 3 Indian Summer, a 5 1/2 furlong turf dash for 2 year olds, completes the day. It does not carry Challenge status.

What Is the Breeders’ Cup Dirt Dozen?

The Breeders’ Cup Dirt Dozen works differently from Win and You’re In. A Dirt Dozen race does not hand out an automatic starting spot. Instead, the first three finishers earn credits toward their Breeders’ Cup pre entry and entry fees.

The series covers 12 North American dirt races, two for each of the six Championship dirt divisions outside the Classic. The Distaff, Sprint, Juvenile and Juvenile Fillies each carry $2 million purses. The Filly & Mare Sprint and Dirt Mile each carry $1 million.

The credits scale with the Championship purse. In races linked to a $1 million division, the first three earn $15,000, $7,500 and $3,750. In races linked to a $2 million division, those credits double to $30,000, $15,000 and $7,500.

Horses can stack credits by placing in more than one Dirt Dozen race, up to the total starting fees for their Championship race. The credits only cover fees for Breeders’ Cup dirt races.

Saturday, October 3: The Frizette at Belmont Park

The $500,000 Grade 1 Frizette, in its 79th running, is the Dirt Dozen race for the Breeders’ Cup Juvenile Fillies this weekend. The juvenile fillies go one mile on dirt at 4:31pm ET, and it is the final Dirt Dozen race on the 2026 schedule.

Because the Breeders’ Cup Juvenile Fillies is a $2 million race, the Frizette winner earns a $30,000 fee credit. Second gets $15,000 and third gets $7,500. Winning the Frizette does not guarantee a starting spot, unlike the Champagne and the other Belmont Challenge races. NYRA’s race calendar makes the difference clear. It tags the Frizette as BC Dirt Dozen and tags the other four as BC Challenge races.

Saturday, October 3: The Delaware Handicap at Delaware Park

Saturday brings a second Dirt Dozen race. Delaware Park postponed its Delaware Handicap card from September 26 because of a Nor’easter and moved the whole program to October 3. That puts the Grade 3 Delaware Handicap for fillies and mares over 1 1/8 miles on dirt on the same afternoon as the Frizette.

The Delaware Handicap is the Dirt Dozen race for the $2 million Breeders’ Cup Distaff, so the top three earn the same $30,000, $15,000 and $7,500 credits. The base purse is $500,000, and it rises to $600,000 if a 2025 or 2026 Grade 1 or Grade 2 winner starts. Between them, the Frizette and the Delaware Handicap close out the 2026 Dirt Dozen series.

Win and You’re In vs. the Dirt Dozen

The easiest way to remember the difference comes down to the finish.

In a Win and You’re In race, only the winner collects. A winner nominated to the Breeders’ Cup gets an automatic starting spot in the matching Championship race, with pre entry and entry fees covered.

In a Dirt Dozen race, the first three all collect. They earn credits toward Breeders’ Cup fees, but none of them receives an automatic starting spot.

A Huge Weekend on the Road to Keeneland

With the Breeders’ Cup now just four weeks away, this is much more than another weekend of stakes racing. Across Friday, Saturday and Sunday, 15 Win and You’re In races at Keeneland, Belmont and Santa Anita hand out automatic berths in 10 Championship divisions. Belmont’s Frizette and Delaware Park’s Delaware Handicap add two Dirt Dozen paydays on Saturday as connections make their final plans.

Plenty of the horses we see this weekend will be back under the lights at Keeneland on October 30 and 31. Follow every step of the road to the Breeders’ Cup with MyWinners.

Bet online at app.mywinners.com, on the MyWinners: Racing & Sports app on iOS or Android, or go here to find your nearest MyWinners or Winners venue in CT.

Image by Jlvsclrk, licensed as CC-by-4.0.