2025: Three-year-old Season
His first race of the year was with the 2000 meter Modified Benchmark 3 Y.O & Over (45-30), on January 25th [6] . Headliner lead the pack until the end, leading by six lengths, but ultimately finishing by four. After his three-year-old debut, he was onto the 1600 meter Chief Commander Classic on March 29. [7] He maintained a four length lead throughout the race, winning the race with a four and a third length gap between him and second placer Showtime. His trainer, John O'Brien was not surprised by his win, saying, "The Commander Classic was won by Headliner, who we all expected to run very well, as he has been unbeaten so far. He did perform really well, and won by four or five lengths." [8]
After the Chief Commander Classic, the next goal was the Trinidadian Triple Crown. The first jewel was the Guineas on May 30 [9] ; Starting on the outside in post seven, the final ruling was Headliner first by ten lengths and a third, with Free Pass in second and Valante in third. The final running time was 1:58.10. [10]
When asked about his performance in the Guineas, jockey Dillon Khelawan stated, "The race took another turn when we were midway down the back-straight as he wanted to go even faster. Going down the back-straight he was travelling so well and going about his business as if it was a one-horse race. Going to the far turn, he was still some ten lengths clear and going extremely well. I thought that coming to the corner I should expect some challenges but that did not happen and Headliner just kept up the gallop all the way up the straight. That is how classy he is." [11] Khelawan also said, "I think he is the best three-year-old in training, and I am looking forward to riding him in the Midsummer Classic and the Derby, the other races of the Triple Crown. He is indeed a very good horse who will take a world of catching in the next four months. He is exceptional." [11]
On 1 August, Headliner ran in the Midsummer Classic [12] , another 1800 meter race, and the second of the Triple Crown races. 1/9 in the betting, Headliner took first by eight lengths.
Trainer John O'Brien said about the colt's performance, "He is a good horse and has won all his races in superb fashion. There is the Derby to come, and it will take a super-performance by another three-year-old to stop him from winning." [13] His owner, Mrs. Diane Scott, also added, "He is amazing. He goes off fast and keeps running." [13]
On September 24th Headliner won the Trinidad Derby [14] , the final leg of the Trinidadian Triple Crown. He finished the race twelve lengths and a half over second place colt Have A Great Day.
Headliner was jockey Khelawan's first Triple Crown success [15] . "This was not easy, winning a Triple Crown is not easy, and it took months of hard work and commitment to achieve the success that Headliner has had during this season," [16] said Khelawan, "He broke well and I made all the running. He went clear going down the back and was travelling best of all coming to the corner. He ran on well to the line. I never doubted he would win the Triple Crown, and he won in style. He will continue to improve." [16] Khelawan also added, "He has shown remarkable improvement, and will go well in his next contest and maintain his unbeaten record." [16]
On December 6th Headliner ran in the Stewards Cup, placing second to Hello World by five lengths, making the race his first loss in his career. [17]
