How to Turn a $5 Horse Bet Into $100

Gear up for the Kentucky Derby with these betting tips.
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Cheryl Ann Quigley /

It's May, and the sound of thundering hoof beats is in the air. The Kentucky Derby is right around the corner, followed by the remaining races toward the coveted Triple Crown. Do you think you can turn that $5 bill in your pocket into $100 or more? Here are a few horseracing tips to keep in mind as you trot up to the horse betting window at Churchill Downs or log on to your favorite wagering website.

Size Up the Odds
Cheryl Ann Quigley /

Size Up the Odds

When you've narrowed down the field to a few horses you like, it's time to find out what the experts think of your choices. Check the morning line — the odds assigned to each horse by professional racetrack handicappers before anyone starts betting on the race.

This reflects who the handicappers think will win. If Fast Sam has short odds, maybe 2/1, the handicappers think he has a good chance of winning the race. If Slow Poke's morning line odds are 50/1, the handicappers suspect that every other horse in the field will finish ahead of him.

Morning line odds are typically stated right next to the horse's name in the program or online race card with the notation "ML."

How Odds Affect Your Wager
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How Odds Affect Your Wager

Let's say you decide to bet on Fast Sam because he seems like a sure winner at 2/1 morning line odds. If he wins, your $5 wager will return just $15: two times the amount of your bet, plus your original wager.

But if Slow Poke pulls off a miracle at 50/1 and somehow finishes first, your $5 will earn you $255 — 50 times the amount of your bet, plus your wager. The problem with that bet, of course, is that you're more likely to be holding a worthless betting ticket in your hand when the race is over rather than a wad of cash. The experts made him a 50/1 longshot for a reason — he's going to be racing against far better steeds.

The question then becomes whether you want to play it safe or go for a significant payout. Even a "chalk" — a horse that is considered so good he's going off at even-money odds or less — will give you a return on your investment if he wins. It just won't be in the neighborhood of $100.

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Keep Your Eye on the Tote Board
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Keep Your Eye on the Tote Board

The morning line is rarely, if ever, an exact reflection of what the horse will eventually pay if he wins. As race time approaches, each horse's odds will shift upward or downward a little as people all over the country — and in the case of the Derby, all over the world — bet on him.

Keep your eye on the tote board and the up-to-the-minute odds as the race approaches. It's that big sign in the infield if you're actually at Churchill Downs, typically lit up with flashing lights. If you're wagering online, you can check current odds right next to the horse's name on the race card.

Post time betting odds reflect actual gambling activity on each horse. As more bets are placed on him, his odds will become shorter. If bettors decline to wager on him, his odds will grow longer.

You're paid based on post time odds if you win, not what the experts thought when they arrived at the morning line. If bettors see something they like in Slow Poke and bet his odds down to 30/1, your $5 winning ticket will pay $155, not $255, no matter what the morning line said.

Here's a tip: If Slow Poke drops from 50/1 betting odds to 20/1 odds or less in a matter of seconds, this means someone somewhere has just put a significant wager down on him, maybe even in the millions. He either knows something that you don't, or he's had one too many mint juleps.

Playing It Safe
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Playing It Safe

"Straight" bets are your least complicated option and they're the safest. These involve wagering that your horse will win, place or show, meaning that he'll come in first, second or third, respectively.

If you wager on him to win and he does indeed win, so do you. If he comes in second or third, you lose. But if you bet on him to place, you'll win money if he either wins or comes in second, and if you bet on him to show, you'll win money if he comes in first, second or third.

Of course, there's a caveat. The betting odds on a horse are "win odds." This is what he pays if he actually wins. The payouts for second and third place finishes depend on how many other people also wager on him to place, as well as which horse finishes ahead of him, so they're much more difficult to calculate.

Suffice it to say that winnings to place are always less than they would be if the horse had won. A third place finish pays even less than a second place finish.

The bottom line is that you're unlikely to win $100 or more if you bet on Fast Sam to show, because even if he wins or comes in second, you'll receive only his third-place winnings. And remember, he went off at 2/1 odds, so he's not paying much to begin with. Slow Poke would pay much better on a show bet because of his long odds, but not $100.

The “Across the Board” Bet
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The “Across the Board” Bet

So how do you place a straight bet to capitalize the most on your wager? One option is to bet your horse "across the board."

This means betting on the horse to win, place and show. It's technically three separate bets, so the cost of your wager has just increased from $5 to $15. But if your horse wins, you'll collect three times — on the win bet, the place bet and the show bet — and each payout will, of course, be more than your $5 wager.

You may lose some money if he comes in third, however, because you wagered $15 to cover all possibilities but you would only collect the third place payout. Fast Sam might pay $6.50 on a $5 bet to show, so you'd lose the difference. Then again, if Slow Poke comes in third and you bet him across the board, you may very well recoup your initial $15 because of his long odds. You just won't win $100.

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The Exacta
Cheryl Ann Quigley /

The Exacta

"Exotic" bets pay the most for a reason — they're hard to hit. They involve betting on more than one horse, so Fast Sam and Slow Poke would both have to finish in the money for you to win.

Betting an exacta means selecting the first and second place horses in order, and it will typically pay much more than winning straight bet tickets on either or both horses. The win would be significant, well over $100 on a $5 exacta bet if Slow Poke managed to finish first, but it would still pay handsomely if he finished second.

And here's some encouraging news: Churchill Downs, home of the Kentucky Derby, offers $1 exacta boxes. You can bet five different combinations of horses on that $5 bet to increase your chances of winning $100 or more.

Let's say you've added I'm Pretty Good to the horses you like. You might bet an exacta with Fast Sam and I'm Pretty Good, one with Fast Sam and Slow Poke, one with I'm Pretty Good and Slow Poke, and maybe throw in a couple more horses for good measure. The average $1 Kentucky Derby exacta payout has been $181 since 2010, so you could very well turn that $5 into something significantly more.

Other Exotic Bets
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Other Exotic Bets

You can choose from a few other exotic bets if you're feeling solid about your horses and want to win a lot rather than play it safe. Betting a trifecta means selecting the top three finishers in order. It's hard, but it pays a lot more than an exacta.

The superfecta is the granddaddy of them all, one of the most difficult wagers to win in horseracing. It involves picking the top four horses in order. But if you're correct — and depending on the odds of the horses involved — you may be able to buy that new car you've always wanted.

Then there's the daily double. This involves picking the winners of two consecutive races, usually the first and second of the day, then the third and fourth races and so on. If you can pick the winner of the Derby plus the winner of the race either immediately before or after the Derby — depending on what doubles Churchill Downs makes available that day — you could potentially hit $100 on a $5 wager. A daily double at Saratoga paid $72.50 on a $2 bet last season.

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Boxing Your Single-Race Exotic Bet
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Boxing Your Single-Race Exotic Bet

A successful exacta, trifecta or superfecta depends on picking your horses in the exact order of finish. That's pretty tough to do. But you can "box" your horses to give yourself a better chance at winning.

This means placing your bet to cover any order of finish. You might bet an exacta using Fast Sam and I'm Pretty Good with Fast Sam to win and I'm Pretty Good to place, then box the wager so you're covered if the opposite happens and I'm Pretty Good edges Fast Sam out by a nose.

If you didn't box your bet, you'd lose thanks to I'm Pretty Good's last-second winning lunge, and that would be painful indeed. But boxing wagers is like betting across the board — it's actually a series of separate bets: $5 on Fast Sam and I'm Pretty Good, then another $5 on I'm Pretty Good and Fast Sam, in that order.

This could get pretty expensive with trifectas and superfectas, because you'd have to cover a lot of combinations. For example, boxing four horses on just a $2 trifecta wager means putting down $48.

But if the odds of all the horses are in your favor, it can result in a nice pay day. And the possibility of winning a big payout by a hair might make it worth the risk.

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About the Author

Beverly Bird

Beverly Bird is a New Jersey-based writer specializing in personal finance and law. She has more than 30 years’ experience, including numerous published books. She offers personal finance workshops for single and divorced parents.

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