Entering a Kentucky Derby contest is an excellent way to make the 152nd edition of the “Run for the Roses” even more exciting! The top horse betting sites have released a variety of free Kentucky Derby contests with real cash prizes, and The Sports Geek has also gotten in on the action!
With little to lose and possibly thousands of dollars to win in cash rewards, this is a great opportunity for horse racing experts and beginners alike. I explore the best Kentucky Derby 2026 contests online, how to play, rules, prizes, and more below!
| CONTEST | DETAILS |
|---|---|
| TSG $500 Kentucky Derby Win, Place, Show Pick’em | Read More |
| BetOnline $10,000 Kentucky Derby First and Last Contest | Read More |
| Sportsbetting.ag $10,000 Kentucky Derby First and Last Contest | Read More |
TSG $500 Kentucky Derby Win, Place, Show Pick'em Contest
The Sports Geek is featuring an exclusive contest for Kentucky Derby bettors that is simple to play and free to enter!
All players have to do is correctly predict the top three finishers in the 152nd Kentucky Derby in order, for a chance to win an Giftogram gift card worth $500! You can also pick certain props, such as the over/under of the winner’s post position, over/under on the winning time, the nationality of the winning jockey, and more!
How to Play
1. Head to the Contests tab at The Sports Geek, at the top of the page, hover over and click “Kentucky Derby Win, Place, Show Pick’em Contest“.
2. Click the “Play Now” button, and select the top three finishers in order, along with any other props you’d like to answer.
3. Once your picks are submitted, you’ll have to input your email address and agree to the terms and conditions of the contest.
4. This contest is 100% free to play as long as you are 21 years old and from the continental United States or Canada!
5. Picks for the contest can be made until the start of the 152nd Kentucky Derby on Saturday, May 2, 2026, at 6:57 p.m. ET.
Gift Card Prizes
Only 100% correct entries will be accepted for a chance to win a $500 gift card from Giftogram! In the case of ties, the accepted players will have to answer a tiebreaker question when submitting their entry.
BetOnline $10,000 Kentucky Derby First & Last Contest
BetOnline continues its impressive free contest offerings with the $10,000 Kentucky Derby First & Last contest! It sounds simple enough, right?
Contestants will be asked to correctly predict which horse will finish first and which horse will finish last in the 152nd Kentucky Derby. It does not matter where the rest of the field finishes in the race.
The only goal is to pick the horse to cross the wire first and last. It’s quick, easy, and doesn’t require any special horse racing betting strategy knowledge to get started!
How to Play
1. Register for an account at BetOnline.
2. Navigate to the BetOnline contests page after you’ve opened your account.
3. Select the $10,000 Kentucky Derby First & Last contest.
4. Pick which horse you believe will win the 152nd Kentucky Derby, and then make your prediction for the last-place finisher.
5. Make at least a $5 wager at the Racebook, or in the Horse Racing section at the Sportsbook, on the Kentucky Derby at BetOnline to be eligible for a cash prize.
6. Picks for the contest can be made until the start of the 152nd Kentucky Derby on Saturday, May 2, at 6:45 p.m. ET.
Cash Prizes – Win Share of $10,000
BetOnline will use a simple formula for splitting the prize pool. You need to get at least one pick right to win a reward, based on the following terms:
| Share of Cash Pool | Result |
|---|---|
| $5,000 | All qualifying players who pick both the winner and last-place finisher. |
| $3,000 | All qualifying players who pick only the winner. |
| $2,000 | All qualifying players who pick the last-place finisher. |
If you are one of the winners, you will receive your prize in your account by Monday, May 4, 2026, by 6:00 PM ET.
SportsBetting.ag $10,000 Kentucky Derby First & Last Contest
Leading online betting site SportsBetting.ag is offering their own $10,000 Kentucky Derby First & Last contest, which is pretty much the same as what BetOnline has to offer!
If you are confident in your Kentucky Derby 2026 predictions, I suggest using the same picks for both contests to maximize your potential profits.
If you’re not too confident in your picks, you could enter both contests and go for different outcomes. Another alternative is to repeat the pick you’re confident in and switch the other one.
No matter what you decide, here’s how to enter this Kentucky Derby contest.
How to Play
1. Register for an account at SportsBetting.ag.
2. While logged in, head to the SportsBetting.ag contests page.
3. Click on the $10,000 Kentucky Derby First & Last contest.
4. Select which horses you believe in the race will win and finish last.
5. Make at least a $5 wager at the Racebook, or the Horse Racing section of the Sportsbook, on the Kentucky Derby to qualify for cash prizes.
6. Picks for the contest can be made (and changed) until the start of the 152nd Kentucky Derby at 6:45 p.m. ET.
Cash Prizes – Win Share of $10,000
SportsBetting.ag’s official payout structure for the Kentucky Derby First & Last contest is here, and the prize pool is $10,000.
| Share of Cash Pool | Result |
|---|---|
| $5,000 | All qualifying players who pick both the winner and last-place finisher. |
| $3,000 | All qualifying players who pick only the winner. |
| $2,000 | All qualifying players who pick the last-place finisher. |
Best of luck with all your Kentucky Derby contests and picks in 2026!
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