Entering a Kentucky Derby contest is an excellent way to make the 151st 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 2025 contests online, how to play, rules, prizes, and more below!
TSG Derby Day Trifecta Challenge
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 151st Kentucky Derby in order, for a chance to win an Amazon gift card worth $300!
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 Trifecta Challenge“.
2. Click the “Play Now” button, and select the top three finishers in order.
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 151st Kentucky Derby on Saturday, May 3, at 6:57 p.m. ET.
Gift Card Prizes
Only 100% correct entries will be accepted for a chance to win a $300 gift card from Amazon! In the case of ties, the accepted players will have to answer a tiebreaker question when submitting their entry.
BetOnline $20,000 Kentucky Derby First & Last Contest
BetOnline continues its impressive free contest offerings with the $20,000 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 151st 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 $20,000 Kentucky Derby First & Last contest.
4. Pick which horse you believe will win the 151st Kentucky Derby, and then make your prediction for the last-place finisher.
5. Make at least a $10 wager 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 151st Kentucky Derby on Saturday, May 3, at 6:45 p.m. ET.
Cash Prizes – Win Share of $20,000
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 |
|---|---|
| $10,000 | All qualifying players who pick both the winner and last-place finisher. |
| $5,000 | All qualifying players who pick only the winner. |
| $3,000 | All qualifying players who pick the last-place finisher. |
| $2,000 | All qualifying players who incorrectly pick both the winner and the last-place finisher. |
Note that the last-place horse must cross the finish line. Horses who receive a DNF do not qualify.
SportsBetting.ag $20,000 Kentucky Derby First & Last Contest
Leading online betting site SportsBetting.ag is offering their own $20,000 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 2025 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 $20,000 Kentucky Derby First & Last contest.
4. Select which horses you believe in the race will win and finish last.
5. Make at least a $10 wager on the Kentucky Derby to qualify for cash prizes.
6. Picks for the contest can be made until the start of the 151st Kentucky Derby at 6:45 p.m. ET.
Cash Prizes – Win Share of $20,000
SportsBetting.ag’s official payout structure for the Kentucky Derby First & Last contest includes $20,000 up for grabs! The split of the pool followed the payout structure below:
Share of Cash Pool Result $10,000 All qualifying players who pick both the winner and last-place finisher. $5,000 All qualifying players who pick only the winner. $3,000 All qualifying players who pick the last-place finisher. $2,000 All qualifying players who incorrectly pick both the winner and the last-place finisher.
Note that horses who DNF are not considered last place. The horse who crosses the finish line last is deemed last place for the purposes of the contest.
Best of luck with all your Kentucky Derby contests and picks in 2025!
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