Kentucky Derby Matchups Another Way To Cash In On The Run For The Roses

FairwayJay chips-in more Kentucky Derby coverage, insight and Match-Up Betting options for the 2021 Run for the Roses.

As OSGA colleague Glenn Greene notes in his Kentucky Derby coverage, Win or Lose, it's great to feel the unique energy and excitement return to Churchill Downs this year for the Kentucky Derby on the first Saturday in May. Glenn and others are Highly Motivated as they shoot for a Derby winner and bigger payouts in the vertical and horizontal wagers. 

But along with the Exotic bets and the most popular Win wagers on the Kentucky Derby, some leading online sportsbooks get more creative with other wagering options leading up to post time at 6:57 p.m. ET on Saturday, May 1. 

Offshore Gaming Association top-rated William Hill offers Kentucky Derby horse match-ups, and so does leading online sportsbook BetOnline. Compare the match-ups and odds, and I've noted a few recent changes in odds at William Hill for bettors interest. 

William Hill 

Essential Quality (-155) vs Hot Rod Charlie (+125) 
Essential Quality (-155) vs Rock Your World (+125)
Known Agenda (-135) vs Highly Motivated (+105)
Rock Your World (-120) over Known Agenda (-110)
Hot Rod Charlie (-130) vs Known Agenda (+100) 
Hot Rod Charlie (-145) vs Highly Motivated (+115)
Hot Rod Charlie (-130) over Rock Your World (+100) 
Highly Motivated (-115) vs Medina Spirit (-115)
Highly Motivated (-130) vs Mandaloun (+100) 
Saint Hood (-145) vs Hidden Stash (+115)  - was -120  
Hidden Stash (-115) vs Helium (-115)  
Soup and Sandwich (-145) vs Bourbonic (+115) - was -130  
Super Stock (-140) vs Bourbonic (+110) 
Super Stock (-130) vs Soup and Sandwich (+100) 
Super Stock (-130) vs Soup and Sandwich (+100) 
Dyanamic One (-115) vs King Fury (-115) 
Midnight Bourbon (-135) vs King Fury (+105) 
Midnight Bourbon (-130) over Dynamic One (+105) 
O Besos (-115) vs King Fury (-115) 
O Besos (-115) vs Dynamic One (-115) 
Midnight Bourbon (-125) vs O Besos (-105) 
Mandaloun (-135) vs Medina Spirit (+105)


Essential Quality (-175) vs Known Agenda (+137)
Essential Quality (-160) vs Rock Your World (+125)
Rock Your World (-122) vs Known Agenda (-108)
Rock Your World (-130) vs Hot Rod Charlie (-101)
Known Agenda (-120) vs Hot Rod Charlie (-110)
Known Agenda (-137) vs Highly Motivated (+105)
Hot Rod Charlie (-140) vs Highly Motivated (+108)
Hot Rod Charlie (-150) vs Medina Spirit (+117)
Highly Motivated (-112) vs Medina Spirit (-108)
Medina Spirit (-133) vs Mandaloun (+102)
Dynamic One (-115) vs Midnight Bourbon (-115)
Dynamic One (-120) vs O Besos (-110)
Super Stock (-135) vs Soup and Sandwich (+104)
Bourbonic (-135) vs Keepmeinmind (+104)
Brooklyn Strong (-128) vs Like the King (-103)
Helium (-120) vs Sainthood (-110)
O Besos (-125) vs Midnight Bourbon (-105)

Kentucky Derby betting tipsI played Rock Your World (+100) over Hot Rod Charlie, and note the difference in odds between William Hill and BetOnline in that matchup. Rock Your World is a -130 favorite at, but an underdog at William Hill. I trust his strong Santa Anita Derby win is just the start of bigger things ahead for Rock Your World. The big striding Candy Ride colt knocked out strong pace figures over the opening mile on a deeper Santa Anita surface, and then kept on running fast to the finish and blew away the field including favorite Medina Spirit. Note strong stretch rider Joel Rosario has jumped off Hot Rod Charlie from the Louisiana Derby win to ride Rock Your World in the Derby.  With Caddo River now out of the Derby, Rock Your World should have a pace advantage up front. I'm hopeful his lack of foundation and no racing as a 2-year-old is more like Triple Crown winner Justify's result than potentially being a one-hit wonder.  

Some sharp bettors that are bullish on Highly Motivated are likely betting him as underdog against Known Agenda in the head-to-head match-ups. I'm sticking with Known Agenda, but not in the match-ups as I don't see as much to like. The poor No. 1 post as not preferred for Known Agenda, although the new gate change allows more room breaking from the rail. He'll hopefully settle back and save ground with top jockey Irad Ortiz getting a big run from him starting on the far turn despite getting some kickback. I've got win exposure already on Known Agenda at 10/1 odds, and will hope he prevails. 

Kentucky Derby Betting Coverage

I've been covering the Kentucky Derby from gate to wire for other major betting companies, platforms and media outets. From longshots to leading contenders, I included a brief overview of each horse in a Kentucky Derby Betting Guide, and continue to get more race insight and information from proven horse handicappers that study the races far more than I do. From pari-mutuel betting and race coverage at Twinspires to TVG, FanDuel and Forbes, I try to chip-in insight and information you can bet on. My coverage, reporting and proven handicapping success, strategies and stories of major sports keeps me on top of more sports and in the game while chipping-in information you can bet on. 

However, I'm not a horse guy or desire to be more involved in a Sport of Kings that is corrupt with drugs and cheating. So when you elect to make a bet on the beautiful equine athletes and their trainers and jockeys, know that you're a Thunder Snow pull up out from the gate (2017 Derby) away from a bad beat in the Kentucky Derby and America's most popular betting race. The favorite Essential Quality (2/1) likely goes off at lower odds as Mattress Mack is back with a record Derby win wager of at least $2 million in the favorite.  

I'll by pulling for a Dynamic One with a Known Agenda in this year's Kentucky Derby. If it's Rock Your World or King Fury to the finish line and the winners circle, I'll be enjoying my post race parade as well.

You can bet on it. 

FairwayJay is a proven sports handicapper and is recognized as one of the sports industry's most insightful analysts. He chips in additional sports betting coverage and reporting on industry news and events. Read more great insights from FairwayJay and follow him on Twitter: @FairwayJay   

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