We’re back with the next instalment of the most electrifying moments in horse racing history.

Last week we counted down some of the most unforgettable moments, and now we’re unveiling the top 5 moments that left a lasting impact on the sport in 2025.

From shocking upsets to record-breaking performances, these moments had fans on the edge of their seats.

So without further ado, let’s dive into the top 5 moments.

1. HURRICANE MELISSA DEALS BLOW TO JAMAICA’S HORSE RACING

Hurricane Melissa slammed Jamaica on October 28, 2025 leaving a trail of destruction, including significant damage to Caymanas Park, the island’s premier horse racing venue. The storm’s fury resulted in a temporary suspension of live racing, dealing a major blow to the industry, with estimated losses exceeding $200 million. The damage was extensive: five stables were hit, and electrical, structural, and technological issues needed urgent attention. Repair crews sprang into action, working tirelessly to restore the facility and its Off Track Betting network. Despite the chaos, the racing surface emerged unscathed, ready for horses to get back to work. And work they did — live racing roared back to life on Saturday, November 15, 2025, just over two weeks after the storm.

2. RIDEALLDAY WINS US$300,000- MOUTTET MILE

The stage was set for a thrilling showdown in the fourth staging of the prestigious Mouttet Mile on Saturday, December 6, 2025. With a US$300,000 purse on the line, the largest in the English-speaking Caribbean, the atmosphere was electric, and the stakes were higher than ever. In a commanding performance, Rideallday, trained by Philip Feanny and ridden by Javier Castellano, destroyed rivals by 9 lengths in the Graded Stakes contest for three-year-olds and upward over one mile (1,600m). The winning time was 1:36.4 (23.1 x 45.0 x 1:10.0), a new stakes record.
Rideallday’s Mouttet Mile triumph was a jaw-dropping, edge-of-your-seat spectacle. Fresh off a length-and-a-quarter win in the Port Royal Sprint, this horse showed he’s not just a flash in the pan — he’s a force. With grit etched on his face, Rideallday played the waiting game perfectly, biding his time through the half-mile turn. Then, like a bullet, he unleashed the afterburners in deep stretch, leaving rivals in the dust. Seven wins from eight starts this season, and the Horse of the Year title is practically his to claim.

3. MIDNIGHT FLIGHT CARRIES CARDENAS TO 800TH VICTORY

On Saturday, September 27, 2025 the winners’ enclosure at Caymanas Park erupted in jubilation as Dick Cardenas — the whip-smart jockey with a story etched in triumph – rode Midnight Flight to victory, clinching his 800th career win in Jamaica. This landmark was achieved in the ninth race, a three-year-old and upward claiming ($1.5m-$1.2) over 5 furlongs straight. Trained by Byron Davis,
Midnight Flight won the race by 1½ length in 59.3 seconds. Cardenas’s path since debuting in 2008 had been paved with grit, passion, and an unwavering gaze towards greatness. He won his first race aboard St Bess, trained by Percival Hussey, at odds of 19-1. Cardenas spoke with heartfelt conviction after Midnight Flight propelled him to his 800th career win. His words reflected the dedication behind this milestone. “It wasn’t easy to win 800 races. I worked very hard for this and so I am very happy that I could win my 800th here at Caymanas Park. To be honest, I never really thought that I would have won so many races here. And so I must thank the owners, trainer, grooms, everybody that supported me during my career. This [Jamaica] is my second home. I met my wife here, and I really like Jamaica,” Cardenas said.

4. HALLEDEEN MAKES HISTORY WITH 500TH WIN AND JAMAICA DERBY TITLE

Jockey Robert “Hard Ball” Halledeen etched his name in the record books on a memorable day at the track on Wednesday, August 6, 2025. Halledeen’s remarkable achievement began with a milestone moment: riding his 500th career winner aboard H Two O, trained by Jason DaCosta, in the Independence Day Stakes Trophy. H Two O, a three-year-old American-bred chestnut colt, won the Restricted Allowance II contest over 7 furlongs by 8 ½ lengths in a smooth 1:26.3. The stage was earlier set for Halledeen’s day with a win on Girvano in the $1.25-million Emelio “Bimbo” Rodriquez Trophy earlier. As Halledeen stood in the winner’s circle, basking in the glory of his 500th career win, he couldn’t help but feel a sense of gratitude and humility. For Halledeen, the milestone was more than just a number — it was a testament to the countless hours he’d spent honing his craft, the sweat and tears shed, and the unwavering support of his loved ones. But Halledeen wasn’t done yet. The very next race, he teamed up again with DaCosta and I Dream Again to win the Jamaica Derby. Owned by Derrick Smith, I Dream Again, under strong urgings, rallied in deep stretch to beat Burning Hedge (Dick Cardenas) by a length in the 105th running of the $7.5-million blue riband event over 12 furlongs (2,400m). The crowd was on its feet, cheering on the horses as they thundered down the stretch. I Dream Again and Burning Hedge were nose to nose, with the outcome hanging precariously in the balance. Burning Hedge pointed on I Dream Again, but Halledeen wasn’t done yet. He urged I Dream Again forward, and the horse found an extra burst of speed, rallying to cross the wire a length ahead of Burning Hedge. Pretty Perfect (Oneil Mullings) finished third. The feeling of triumph still hadn’t fully sunk in for Halledeen, but one thing was certain — he was overjoyed for everyone involved with I Dream Again. His happiness extended far beyond his own family to Jason DaCosta’s family, Mr Smith and his family, and the entire team of supporters and fans who had backed the talented colt. “The feeling hasn’t soaked in as yet. I am happy for my family, for Jason’s family, for Mr Smith and his family, all
I Dream Again’s supporters, and fans. I am really grateful and thanks everyone for their input,” Halladeen said.

5. TENECA WOLFE’S HISTORIC WIN AT CAYMANAS PARK

In a heart-stopping, awe-inspiring moment that will be etched in the annals of horse racing history, Teneca Wolfe, a trailblazing Canadian-based jockey, rode her way to glory at Caymanas Park on July 19, 2025. With her ailing father, Trevor Davis, watching from the sidelines, Wolfe rode the Richard Azan-trained ButterCup to a thunderous 5 ¾-length victory in the $750,000 Jamaica Jockeys’ Guild Trophy, a 7-furlong Restricted Allowance V contest for four-year-olds and upward, becoming the first black female jockey from Canada to win a race at Caymanas Park. This wasn’t just a win; it was a dream fulfilled, a testimony to Wolfe’s unwavering dedication, unrelenting passion, and unshakeable resolve. As she celebrated her victory, Wolfe’s father was brought to the winners’ enclosure, creating a poignant moment that will forever be remembered as one of the most emotional moments in horse racing history. Suffering from dementia, Davis had been a constant source of inspiration for Wolfe, who had long dreamed of winning in Jamaica with her father by her side. Wolfe’s ride on ButterCup was a masterclass in skill and finesse, showcasing her exceptional ability to navigate the track and coax the best out of her mount. With a perfect hold and measured tempo, Wolfe set the pace, and ButterCup responded with a scintillating performance, stretching clear by daylight to cross the finish line in emphatic style. ButterCup ( Conquest Cherimash – Shahar) won in a time of 1:31.4 (24.4 x 49.4 x 1:17.2) ahead of Successful Man (Shane Ellis) and
Never (Anthony Allen).

Broadcasting boxeson the roof at Caymanas Park suffered damages by Hurricane Melissa on Tuesday, October 28, 2025. (Photo: Karl Mclarty)

Jockey Dick Cardenas celebrates his 500th career winner in Jamaica on Saturday, September 27, 2025. (Photo: Garfield Robinson)

LOVE AND PRIDE! Jockey Teneca Wolfe (right) shares a sweet moment with her dad Trevor Davis after winning her first race in Jamaica aboard ButterCup on Saturday, July 19, 2025. (Photo: Naphtali Junior)

Rideallday (Javier Castellano) romps home in the US$300,000-Mouttet Mile on Saturday, December 6, 2025. (Photo: Naphtali Junior)

New ownership, Cassiopeia Inc, celebrate Rideallday’s victory in the US$300,000-Mouttet Mile on Saturday, December 6, 2025. (Photo: Naphtali Junior)

Jockey Robert Halledeen stands tall in the saddle as he crosses the finishing line in first place aboard I Dream Again in the 105th running of the $7.5-million Jamaica Derby Classic at Caymanas Park on Wednesday, August 6, 2025. (Photo: Naphtali Junior)

ButterCup is pushed out by Teneca Wolfe to win the Jamaica Jockey’s Guild Trophy on Saturday, July 19, 2025. It was Wolfe’s first win in Jamaica. (Photo: Naphtali Junior)

H Two O easily wins the Independence Day Stakes Trophy on Wednesday, August 6, 2025, giving jockey Robert Halledeen his 500th career winner. (Photo: Naphtali Junior)