The 152nd Kentucky Oaks is shaping up to be a thriller, and all eyes are on Hall of Fame trainer Todd Pletcher as he chases history. Pletcher, who has famously struggled in the Kentucky Derby with just two wins from 65 starters, is a completely different force in the Oaks. With four wins from 27 starters—tied for third-most all-time—a victory on Friday night would tie him with legends Woody Stephens and D. Wayne Lukas for the most Oaks wins ever.

Pletcher's best shot at that record-tying fifth win comes in the form of Zany, the 4-1 morning-line favorite. This daughter of 2015 Triple Crown winner American Pharoah has been impressive, winning three of her four career starts, including the Grade 2 Demoiselle Stakes at the same 1 1/8-mile distance as the Oaks. Her only blemish? A second-place finish in the Ashland Stakes at Keeneland. But don't let that fool you—Pletcher isn't worried. He attributes the loss to the Ashland's short stretch, which didn't suit Zany's powerful closing kick. "I think it was a good experience for her," Pletcher said, "and I think it hopefully sets her up well for her best performance in here."

If the odds are any indication, the Oaks is a wide-open affair. Six fillies in the 14-horse field are listed between 4-1 and 8-1, including Meaning (5-1), Explora (6-1), Percy's Bar (6-1), Counting Stars (8-1), and Prom Queen (8-1). It's the kind of evenly matched field that makes for heart-pounding racing—and perfect inspiration for your next big day at the track. Whether you're dressing for the winner's circle or just enjoying the race from home, a sleek new racing-inspired outfit can set the mood.

This year's Oaks is historic for more than just the competition. For the first time in 152 years, the race will run in primetime, with a post time of 8:40 p.m. ET. That's a major shift from last year's 5:51 p.m. start, all to accommodate a national NBC broadcast. Industry insiders are already buzzing: if the Oaks thrives in primetime, the Kentucky Derby could follow suit. As for the weather, Louisville is expecting partly cloudy skies, temperatures in the 50s, and zero chance of rain—ideal conditions for a night of unforgettable racing.