Kentucky Oaks 2021 Betting – Top Contenders, Betting Odds, Best Bets


The 2021 Kentucky Oaks takes place on Saturday and gives the sports world a glimpse at some of the top female thoroughbred talent in the world. 14 fillies will go to gate in search of a win in one of the most prestigious races of all for female horses. Betting should be intense, and we’ve got a preview so that you can make your wager at top Kentucky Oaks betting sites with all the necessary information at your disposal.

In terms of popularity among horse races, the Kentucky Oaks stands as one of the most well-known events. That’s in part due to its status as the sister race to the Kentucky Derby, which is also held at Churchill Downs in Louisville, Kentucky, just a short time after the Oaks. The Oaks shines the spotlight on the three-year-old fillies.

While fillies have at times run in (and won) the Kentucky Derby, the best distaff horses are usually pointed to the Kentucky Oaks. With a massive purse and a lot of prestige on the line, there are plenty of obvious reasons why. And this year’s race figures to be a doozy, with a competitive group that should offer plenty of excellent value betting opportunities.

Back to Spring

The 2021 edition of the Kentucky Oaks also represents a return to normalcy of some sorts, as the race returns to its normal spot in the spring. Last year it, along with the Kentucky Derby, was postponed until September. That somehow took some of the glory out of the race, as it came at a time in the season where the best three-year-old fillies had already run a whole gamut of stakes races.

Part of the lure of the Oaks is it represents one of the first major opportunities for these fillies to step into such major competition. This year’s group of 14 entrants features several horses who seem to have what it takes to become superstars in the sport. But Friday’s Oaks will be the true testing ground, with one horse eventually emerging to join a long line of fantastic champions.

We’re here to sort out the contenders from the pretenders with this 2021 Kentucky Oaks betting preview. First, we’ll take an in-depth look at each of the 14 horses who’ll line up on Friday behind the gate. And then we’ll tell you who believe should be on your betting ticket.

2021 Kentucky Oaks Details

  • Where: Churchill Downs in Louisville, Kentucky
  • When: Saturday, May 1, 2021, Post Time of 5:50 PM ET (Race 11 on Churchill program)
  • Who: 14 three-year-old fillies
  • How long: 1 1/8 miles
  • Surface: Dirt
  • Purse: $1.25 million

The 2021 Kentucky Oaks Field

#1 Pauline’s Pearl (Ricardo Santana, Steven Asmussen) 20-1

Trainer Asmussen has scored a pair of Oaks victories in his illustrious career, with the most recent being in Untapable. Pauline’s Pearl shares a sire with that horse in Tapit, so clearly Asmussen would like history to repeat itself here. And there is an outside chance of that happening if this filly continues her upward trajectory.

First of all, her stalking style is a good fit for the 1 1/8 distance of the Oaks. On top of that, her speed figures have been trending up throughout her career, peaking with her last start. That was when Pauline’s Pearl came up big to win a Grade 3 at Oaklawn to use as a springboard into this race.

Her workouts at Churchill haven’t been all that eye-popping, so that’s a little bit concerning. And she is just two starts removed from being beaten by Will’s Secret, who is an even longer shot than her on the morning line. But Pauline’s Pearl is part of a strong group of mid-priced horses that represents solid value in this race.

#2 Maracuja (Kendrick Carmouche, Rob Atras) 20-1

This will be the first time out of New York and the friendly confines of Aqueduct for this filly. It took her three starts to get her maiden victory, which she achieved in February at a distance of 6 ½ furlongs. Her connections saw how she finished out that race and decided to move Maracuja up to the Grade 3 Gazelle and two turns.

The results were promising enough that she’ll be battling it out against the best fillies in the Oaks. In that race, she had to endure a five-wide journey, but she was still there at the end wining, eventually finishing second at 18-1. She wasn’t all that close to the race winner Search Results, but there was enough there to give Maracuja a look in this one.

The one worry is that it was such a jump in form that she might actually bounce back in the other direction for this race. On top of that, the new surroundings might be a bit of a hindrance. Still, some East Coast love could push the odds down a bit for Maracuja when all is said and done, although it’s not likely to propel her into contention.

#3 Clairiere (Tyler Gaffalione, Steven Asmussen) 5-1

Asmussen’s second entry in the Oaks gets a new set of hands in Gaffalione, which sometimes can be a boost to a horse. Not that Clairiere has exactly been lagging in her previous races. The filly by Curlin comes in with four races under her belt and has never finished worse than second.

She has actually developed a budding rivalry with Travel Column, whom she’ll meet again in the Oaks. In her first graded stakes try as a two-year-old, Clairiere endured a tough trip at Churchill, grabbed the lead, but was caught by Travel Column at the end. But she rebounded in her first start this year to knock her foe off in a Grade 2.

That was followed by another second behind Travel Column in her last start at Fair Grounds. It’s enough to make you think that these two are keeping taps on each other while these races are going on. But Clairiere will have many more top horses to worry about if she wants to be crowned Oaks champion, which will probably require a bit more of an alert start so that her closing kick pays dividends.

#4 Crazy Beautiful (Jose Ortiz, Kenneth McPeek) 15-1

While trainer Ken McPeek is still looking for his elusive first Oaks win, jockey Jose Ortiz scored with Serengeti Express just two years ago. They’re the connections for an avid campaigner who goes after it with gusto just about each and every time out. The one time that Crazy Beautiful stiffed was in the Breeders’ Cup Juvenile Fillies last year, but most of the top horses from that race are absent here anyway.

In six other races, Crazy Beautiful has three wins and three places. But she was on a four-race losing streak until lining up in the Gulfstream Park Oaks in March. That’s when she put on by far the best effort of her career, weaving between horses beautifully before going away for the victory.

That was the first time that Ortiz rode her, so it could be a case of a jockey and a horse finding a nice connection. She hasn’t been at Churchill since a second in a Grade 2 last September, but she did start her career with two wins at Ellis Park in Kentucky. Her return could be a triumphant one if the pace is hot enough early for Crazy Beautiful to unleash her closing kick.

#5 Pass The Champagne (Javier Castellano, George Weaver) 15-1

Veteran jockey Javier Castellano has one Oaks victory to his credit with Cathryn Sophia in 2016, while trainer George Weaver is looking for her first score in this prestigious race. Weaver only took over as trainer for Pass The Champagne this year. But he has found something in the filly, who might be lightly raced but has some intriguing recommending qualities.

In her second career race, she beat a field of ten at Gulfstream for her maiden victory. She then headed to Keeneland for the Grade 1 Ashland in her first try around two turns. And after banging into the gate at the beginning of the race, Pass The Champagne found herself on the lead with a big move into the second turn.

The move may have been a bit early, because it left her vulnerable to Malathaat, who figures to be the Oaks favorite and eventually beat her by a head. Still, that was an impressive effort for her first stakes try like that, and she seems to have the right kind of style to figure in here. Pass The Champagne looks like a long shot who could be a factor.

#6 Travel Column (Florent Geroux, Brad Cox) 3-1

Trainer Brad Cox is turning into one of the dominant figures in the sport, as he’ll be sending out several top competitors in the Kentucky Derby later in the day. He has also been on a roll in the Oaks of late, winning two of the last three editions. Travel Column looks like the better chance of his two entrants here to give him another score.

Jockey Florent Geroux has also been aboard those recent Oaks winners for Cox, and he has been with Travel Column since she started her career. We mentioned above about the way she keeps hooking up with fellow Oaks entrant Clairiere. What stands out about Travel Column has been her versatility in terms of style.

She has scored graded stakes wins both as a stalker and as a closer. And he maiden win back in her debut at Churchill last September was as a frontrunner. That kind of flexibility should serve her well in a race with such a crowded field where anything might happen early on.

#7 Ava’s Grace (David Cohen, Robertino Diodoro) 50-1

This filly has all the makings of a long shot. The connections aren’t exactly in the limelight, the pedigree is less than substantial, and the results have been less than impressive. But if you want to strain a little bit, you could find some reasons to consider Ava’s Grace.

First of all, her lone career win came in Kentucky at Ellis Park last July. In addition, she is coming off her best effort yet, a second in a Grade 2 behind Pauline’s Pearl in the Fantasy at Oaklawn. And, as a frontrunner, Ava’s Grace might have a somewhat unique style that could sneak up on some people.

Her speed figure in the last race is at least in the ballpark with some of others in here. But while he frontrunning style could be a benefit in that she might be able to get to the front, it’s a hindrance because it will make it hard for her to get the extra distance. Most likely, you’ll see Ava Grace briefly surge to the front bunch of leaders before quietly bowing out when they turn for home.

#8 Moraz (Flavien Prat, Michael McCarthy) 30-1

The jockey switch to Flavien Prat seems to be an effort to liven up this filly and perhaps provide a spark that could make her a live long shot. What’s interesting about her is the fact that, as a West Coast invader, there isn’t a lot of context here. She hasn’t really faced any of these horses in this field recently, which means that there isn’t a lot for handicappers to draw on in terms of comparisons.

The big concern is that her races on the West Coast were populated by extremely small fields. In her last three races, the biggest field faced by Moraz was five horses. What will she do when she lines up smack dab in the middle of a 14-horse logjam on Saturday afternoon?

In terms of results, Moraz was trending in a pretty good direction with her speed figures until a lackluster effort her last race in the Santa Anita Oaks. Can she find the form that made her an eleven-length maiden winner in January? It seems like the caliber of competition will be too much for her in this one.

#9 Coach (Luis Saez, Brad Cox) 50-1

Trainer Brad Cox’s second entry needs a serious form reversal to have any kind of a chance here. As a two-year-old, Coach started out her career like a house on fire, winning the first three, two in Indiana and then an ungraded stakes at Churchill Downs. But once she entered graded stakes action, her fortunes turned.

In three graded stakes efforts, Coach has finished no better than third. And she is still looking for her first win since that winning streak that kicked off her career. Most recently, she ended up 3rd in the Fantasy behind Pauline’s Pearl and Ava’s Grace, two horses that she’ll be facing in this one once again.

There might be some who go all-in on Cox in this race, which might make Coach a sensible exotic betting play. But she just seems to lack the oomph when the race is on the line, at least against graded stakes competition. As a result, she seems like one you can safely eliminate from consideration.

#10 Malathaat (John Velazquez, Todd Pletcher) 5-2

The unbeaten morning-line favorite deserves consideration based on just her connections alone. Trainer Todd Pletcher has won three different Kentucky Oaks, the last coming in 2013 with Princess Of Sylmar, while jockey John Velazquez won the race back in 2004, in conjunction with Pletcher, aboard Ashado. And the duo just might have their most talented entrant yet in Malathaat.
Like many of Pletcher’s trainees, Malathaat began her career in New York, where she won her first three starts. Interestingly enough, one of those was at 1 1/8 miles, which makes her one of the few in this field to have raced at (and conquered) that distance. Her first trip out of the Empire State was a ringing success, as she took the Grade 1 Ashland at Keeneland in her last race.

What was impressive in his race was the length of the drive that she sustained. Malathaat has adjusted beautifully to the extra distance, switching to more of a stalking style that suits two turns better than the front-end speed she used when winning her first two sprints. This will be a tough test and the post isn’t ideal, but she certainly has the target on her tail in this field.

#11 Will’s Secret (Jon Court, Dallas Stewart) 30-1

This filly caught fire following her maiden victory last December at Fair Grounds. Will’s Secret then followed it up with two more wins in a rrow, with the latter coming in a Grade 3 over Pauline’s Pearl. Trainer Dallas Stewart has high hopes that this could be his first Oaks win since he did it with Lemons Forever all the way back in 2006.

For that to happen though, Will’s Secret is somehow going to have to improve drastically, if her last start is any indication. That’s when she came up a distant third in the Ashland behind Malathaat and Pass The Champagne. When she tried to rally late, there was nothing there, and it looked like she couldn’t hang with the other two.

Quite frankly, that just might be the case for this filly, that she’s just not on that level. Her speed figures have never maxed out at a standard that some of the others in this field have reached. As a result, it doesn’t seem like Will’s Secret will be among the top competitors in this one.

#12 Search Results (Irad Ortiz Jr., Chad Brown) 3-1

The other unbeaten horse in his field, Search Results was unraced as a two-year-old. But that didn’t stop her from hitting the ground running as a three-year-old, ripping off three straight victories. And in each of those races, Search Results has shown the kind of finishing kick that lends to the belief that she’ll make the 1 1/8 miles with no problem.

She started her career with a romping win at six furlongs at Gulfstream. Next up was an ungraded stakes at Aqueduct at a mile, which she handled with aplomb. In the Grade 3 Gazelle, also at Aqueduct, Search Results went off at 1 to 5 and didn’t disappoint, drawing away to win it by 2 ¾ lengths over Maracuja in a command performance.

It’s hard to find anything not to like about this filly, other than perhaps the post position. Still, she has had the far outside post in two of three wins so far, albeit with much smaller fields than the one she’ll face in the Oaks. Throw in perhaps the most impressive speed figures of the entire group and a versatile running style and you can see why this one would be getting attention from the bettors.

#13 Competitive Speed (Chris Landeros, Javier Gonzalez) 50-1

For this filly to be a factor, the pace is going to have to be a blistering one early on, which, from looking at the field and their racing styles, doesn’t seem likely to be the case. Competitive Speed likes to lay back and try to make a belated charge into the ranks. That was the case even when she was a sprinter in one-turn races to start her career.

There’s an argument to be made that she might be better-suited to those types of races. Between November 2020 and January 2021, she scored three straight wins at distances of between six and seven furlongs, all by handy margins. It was only in her last two races that Competitive Speed moved to a distance of a mile or longer.

The results in those two races: a pair of 3rds in Grade 2s. While that’s not embarrassing by any stretch, there wasn’t a point in either of those two starts where Competitive Spirit seemed a threat to win. With the competition only getting better in this race, it seems likely that she’ll finish up the track.

#14 Millefeuille (Joel Rosario, William Mott) 20-1

It’s hard to believe that trainer Bill Mott has never scored a win in the Kentucky Oaks before; the decorated trainer has won just about everything else. He puts Joel Rosario, who rode Millefeuille in the first three races of her career, back aboard to provide a spark. With this filly, the hard part is figuring out which of her last two races to believe.
In a Grade 2 in February at Gulfstream Park, Millefeuille threw in an absolute clunker, finishing seventh in a race where she was bet at 3 to 1. But then she came back a month later at 1 1/16 in the Gulfstream Park Oaks and managed a second-place finish. She actually held the lead after a big move in that one only to cede it late to Crazy Beautiful.

Millefeuille only has one win to her credit, but she does have a pair of seconds in Grade 2s. The post position is obviously a hindrance here, especially because she likes to stalk the pace and will have a hard time finding positioning to do so. It doesn’t like this filly will be the one to get Mott his first ever Oaks victory.

The 2021 Kentucky Oaks Superfecta Pick

The two unbeaten horses in this one seem to be just a notch above the rest. Even though the morning line puts Travel Column in the same boat as the other two, she seems like she might have peaked with the last one and could be going in the wrong direction. But there might be some value elsewhere in the field that could be useful in your tickets at top real money sports betting sites.

In a race where there isn’t a lot of gate speed, Pass The Champagne could be an interesting long shot play. If she can get away cleanly, she’ll have a big post position edge on the two unbeaten fillies. Then it’s just a matter of whether she can hold up late.

What seems likely to happen is that the 1 1/8-mile distance might just catch up to her at the end of the race. That’s when Search Party, who looks maybe like the better of the two spotless horses, will be looming large. It’s Search Party coming up for the win in the 2021 Kentucky Oaks, followed by Pass The Champagne, Malathaat, and Maracuja.

2021 Kentucky Oaks Superfecta Pick –12-5-10-2

Jim Beviglia

Jim Beviglia joined as a staff writer in 2018, parlaying his years of freelance writing into contributions on a number of different topics. He handles the sport of horse racing for and the intersection between the worlds of cryptocurrency and online gambling in a weekly blog.
For his full-time job, Jim handles the television and track announcing duties at a h …

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