The 2025 horse racing season in Jamaica was a wild ride, full of thrilling moments, shocking upsets, and record-breaking wins. But it wasn’t all smooth sailing — controversy and debates made headlines too. Despite the challenges, however, Jamaican horse racing spirit remained unbroken.

TheJamaica Observer’s The Supreme Racing Guide team has curated the top 10 moments of the season, featuring expert analysis and unforgettable moments that captivated the racing community and the public. This list is sure to spark lively discussions and reignite the passion of the season.

So, without further ado, let’s dive into the top six to 10 moments of the 2025 horse racing season. And be sure to tune in to next week’s edition of The Supreme Racing Guide for the top 5.

6. DARBY CELEBRATES 500TH CAREER WIN

Trainer Ryan Darby achieved a monumental milestone on Saturday, August 2, 2025, when his charge All Together crossed the finish line first, marking Darby’s 500th career winner at Caymanas Park. Ridden by apprentice jockey Demar Williams, All Together’s victory came in the $1.05-million Beverly Rhoden Memorial Cup, a maiden condition race for native-bred three-year-olds fillies over 5½ furlongs. All Together won by half-length ahead of Miss Braeton (Oneil Mullings) and Dreamer’s Corner (Omar Walker) in 1:10.1.

As Darby reflected on this incredible feat, his enthusiasm was evident.

“I’m happy and looking forward to another 500. I’ve been telling people that after I reached 499 and my father reached 800, I’ve won a lot of races, so there weren’t any nerves. I didn’t have the material like one time and so it [getting to 500 winners] took a little longer than expected. But I’m rebuilding and rebranding, and I’ll pick up the pace for sure. I have done it before and so I will pick up pace and momentum very soon. I would imagine that my first winner was probably a little bit more emotional but I’m appreciative of this 500 winners. Both my first winner and my 500th winner are great accomplishments, and hopefully, when I reach the 1,000, I’ll celebrate more,” Darby said.

7. MOJITO DELIVERS STUNNING PERFORMANCE TO WIN JAMAICA CUP FEATURE

In a breathtaking display, the Richard Azan-conditioned Mojito outlasted his rivals to claim the $6-million Jamaica Cup on November 16, 2025. The five year-old grey horse, ridden by Raddesh Roman, showcased his exceptional speed and endurance, holding off challengers over the demanding nine and a half furlongs (1,900m) distance. Mojito patiently waited in mid pack behind the early pace, allowing Mamma Mia (Jerome Innis) to lead the charge around the clubhouse turn and down the back stretch. As the field navigated the half-mile turn, Mojito burst through the pack, picking up the lead with Run Julie Run (Dick Cardenas) attached to his inside. Mojito shook off Run Julie Run at the top of the straight and turned on the pressure in deep stretch but despite shortening his stride in the final stages, he held on to secure a length-and-a-half win. Girvano finished second, with Run Julie Run taking third. Mojito’s Jamaica Cup win was a masterclass in patience and power.

8. VETERAN JOCKEY CLIVE LYNCH HITS 500 CAREER VICTORIES ABOARD

Jockey Clive Lynch rode into the history books on Saturday, September 27, 2025, with a triumphant 500th career win aboard Mr Lee in the Reprieve Trophy. The Reprieve Trophy, a Restricted Allowance II contest for native-bred three-year-olds (non-winners of two) and imported three-year-olds and upward (maidens) over 9 furlongs (1,800m), saw Mr Lee winning by a neck. Mr Lee came from behind runners to nip Alchemy of Souls (Robert Halledeen) on the wire, completing the distance in 1:58.4 (24.1 x 47.4 x 1:14.2 x 1:43.4).

“I feel great about this achievement.

I should have done this a few race days back as Mr [Jason] DaCosta gave me a chance to get my 500th win, but it was just unfortunate. Now this 500th win came in such a way that I am grateful of it. I am feeling great, I am feeling good. I must thank trainer Mr Lee Clarke for giving me this 500th win. I mean, 500 races, I give thanks for it, but really and truly I should have gone a lot more. Looking back at my career, I wouldn’t have done anything differently. I have no regrets. There are a lot of jockeys here and very few who had the opportunity or the success to win 500 races. I give thanks and praises. Such milestones don’t come easy, it takes a lot of hard work and discipline and I am forever grateful for this moment. I am looking forward to another 500 wins to make it 1,000 wins. There’s no time for retirement as when the time comes, my body will tell me,” Lynch said.

9. WE JAMMIN REIGNS SUPREME IN WAYNE DACOSTA TWO-YEAR-OLD STAKES

We Jammin, ridden by Omar Walker, swept all before him in a dominant run to win the $4-million Wayne DaCosta OD Jamaica Two-Year-Old Stakes at Caymanas Park on Boxing Day, December 26, 2025. Trained by Peter-John Parsard, the two-year-old chestnut colt covered the one-mile distance in 1:42.2 (25.1 x 49.2 x 1:15.4 x 1:28.3), winning by six lengths. We Jammin sat back in the pack before unleashing a powerful late charge in the stretch to beat favourites Salute The Don (Dane Dawkins) and Fernando (Dane Nelson). This victory marks We Jammin’s second career start, showcasing his exceptional talent and potential. We Jammin is the only local two-year-old to win two races.

10. TIGRAY EXPRESS SHINES — A RARE CLAIMING GEM

At a level where consistency is golden, Tigray Express just turned claiming racing into pure art. The chestnut colt nailed eight wins in nine starts — a rarity among claiming horses — and locked in a fifth-straight victory as well on Saturday, November 22, 2025. The race was an Optional Claiming ($500,000-$400,000) contest that included native-bred six-year-olds and upward (non-winners of four) and native-bred five-year-olds (non-winners of three) over 6 ½ furlongs (1,300m).
Tigray Express broke sharply, assumed the lead early, and never looked back.

He maintained a strong gallop throughout before drawing clear in the straight to win by 9½ lengths in a time of 1:24.0 (24.2 x 49.1 x 1:16.2). High Diplomacy, partnered by Robert Halledeen, chased in vain and had to settle for second, while Wilson, ridden by Oshadane Robinson, finished third. Immediately after the race it was confirmed that Tigray Express had been claimed for $500,000 by trainer Dalton Sirjue on behalf of owner Anthony Chin.

Interest was intense, with 32 claims lodged for Tigray Express. This latest triumph lifts Tigray Express’s overall career record to 14 wins from 54 starts, with total stakes earnings now approaching $8 million. His consistency and ability to deliver under different trainers and riders have made him one of the most sought-after horses on the circuit. Tigray Express’s only loss this season came on May 23 in at a $1-million claiming level where he finished fourth by 7 lengths behind Burning Valor over 7 furlongs.

Alexander Haber (second left), part-owner of Mojito, celebrates after his charge won the $6-million Jamaica Cup on Sunday, November 16, 2025. (Photo: Karl Mclarty)

Mojito (Raddesh Roman) outstays rivals to win the $6-million Jamaica Cup on Sunday, November 16, 2025. (Photo: Karl Mclarty)

Jockey Clive Lynch aboard Mr Lee celebrates his 500th career win in the winners’ enclosure with connections of the horse including trainer Lee Clarke (left) on Saturday, September 27, 2025. (Photo: Garfield Robinson)

Trainer Peter-John Parsard (left) and his charge We Jammin (Omar Walker) after the chestnut colt won the $4 million Wayne DaCosta OD Jamaica Two-Year-Old Stakes on Friday, December 26, 2025. At right is groom Frank Spencer.(Photo: Naphtali Junior)

We Jammin (Omar Walker) on his way to an easy win in the $4 million Wayne DaCosta OD Jamaica Two-Year-Old Stakes on Friday, December 26, 20256. (Photo: Naphtali Junior)

Tigray Express (Raddesh Roman) easily wins the third race on Saturday, November 22, 2025, his fifth consecutive victory and eighth in nine starts. (Photo: Karl Mclarty)