In 2018, he won the Eclipse Award for Outstanding Jockey after leading the jockey list by both number of wins and earnings. He won the Belmont spring/summer and Saratoga meets, the latter highlighted by a win in the Whitney Handicap on Diversify. He earned his 2,000th career win on September 15 aboard Gambler's Fallacy at Belmont Park. He won the Shoemaker Award for outstanding jockey at the 2018 Breeders' Cup after he won two races, the Juvenile Fillies Turf with Newspaperofrecord and the Filly & Mare Sprint with Shamrock Rose, plus scoring five more top four finishes. Ortiz experienced a slowdown in business in the fall of 2019, finishing just ninth in the Belmont meet standings. However, he had an exceptional weekend at the 2019 Breeders' Cup with four winners, including Bricks and Mortar in the $4 million Turf and Vino Rosso in the $6 million Classic. "Some riders have a good rapport with certain horses," said trainer Todd Pletcher. "Irad and Vino Rosso really gelled, you could see there was great chemistry there from the first time he got on him."