Free Picks: 2014 Kentucky Derby Prop Bets & Matchups

David Schwab

Wednesday, April 30, 2014 6:01 PM GMT

The only thing better than trying to pick a winner of the 2014 Kentucky Derby from a field of 20 of the best three-year old Thoroughbreds in the country, is trying to cash-in on any number of prop bets and matchups that are released by the sportsbooks for this event.

Margin of Victory
When you take a historical look at the past margin of victories in the Kentucky Derby, you would find that the most common distance is between two and three lengths. That is why it is little wonder that the best odds on the board at +200 is a margin of victory between 1 and 2 ¾ lengths. In 2012, I’ll Have Another won the Derby by 1 ½ lengths; which was the closest margin of victory in the past eight years. The largest margin of victory during that same time span was Mine That Bird’s impressive 6 ¾ length win in 2009. 

The next best odds on the board at +300 is a margin of victory between 3 and 5 ¾ lengths. I am going the other way in an effort to stretch the value in the odds with a play on ½ to ¾ length at +400 in what should be a very competitive race. I may be going out on a limb with this pick since that last time a Kentucky Derby finished that tight was all the way back in 1998 when Real Quiet won by half a length.


The Winning Time
There is a reason that people refer to the Kentucky Derby as “The Most Exciting Two Minutes in Sports” since that is generally how long it takes these Thoroughbreds to run the 1 ¼ mile distance. 

Orb’s winning time in last year’s race was 2:02.89, which was the slowest time in the last four years. The fastest time in recent memory was Barbaro’s 2:01.36 run to victory in 2006. As you can see there is very little difference between the two which is why the moneyline odds on “OVER or UNDER 2:02.50” are both set at -115.

The correct call in this prop bet hinges heavily on track conditions and the post position of some of the favorites. Right now, the weather forecast is calling for a fast, dry track at Churchill Downs for this race, which combined with the quality of horses in this field should set the stage for a faster than average winning time. It all comes down to a minuscule fraction of time, but I am going with the 'under' in this prop.

 

Betting on Head-to-Head Matchups
One of the best ways to cash-in on a prop bet is to handicap the field and then look for the odds on a head-to-head matchup that are stacked in your favor. By the time Saturday rolls around, Sportsbooks will probably add even more of these types of props to the list, but looking at what is currently posted, I believe I have found one that offers some tremendous value given the current numbers along my personal efforts to handicap this race.

The current moneyline odds for the following matchup favor Vicar’s in Trouble (-180) finishing better that Uncle Sigh (+135). These numbers do not match-up with the current odds to win this race seeing that Vicar’s in Trouble is currently listed at +4200 and Uncle Sigh is listed at +3500. I personally think that Uncle Sigh is going to finish much better than Vicar’s in Trouble regardless what the numbers say as I have narrowed him down to a pool of my top five contenders to win this race. The fact that I can cash-in on a favorable moneyline in a head-to-head matchup is a bonus.