In 1981, Pleasant Colony made his attempt at glory coming off a win in the Wood Memorial, only his second win as a 3-year old. He won the Kentucky Derby by 3/4 lengths and the Preakness by 1 length. In the Belmont, he ran third 1-1/2 lengths behind Summing, who had won his maiden race over Pleasant Colony and came into the Belmont with wins in the Hill Prince and Pennsylvania Derby.
The 1978 Triple Crown runner-up Alydar sought redemption through his offspring Alysheba in the 1987 Triple Crown series. Alysheba's only win as a 3-year-old came off a disqualification, yet he won the Kentucky Derby by 3/4 lengths and the Preakness by a 1/2 lengths. Bet Twice, 2nd in the Derby and Preakness, romped to a 14-length win in the Belmont with Alysheba finishing 4th. Alysheba and Bet Twice would go head to head a total of 7 times with 3 wins each.
In 1989 Sunday Silence won all the big west coast preps. He went on to win the Kentucky Derby by 2-1/2 lengths and the Preakness by a nose, both over Easy Goer who had won the big east coast preps. In the Belmont, Easy Goer got his revenge and beat Sunday Silence by 8 lengths. They met once more with Sunday Silence winning the Breeders' Cup Classic by a neck.
In 1997, Silver Charm won the Kentucky Derby and Preakness by a head. He was leading down the stretch in the Belmont only to be caught by Touch Gold, finishing 2nd by 3/4 length. Touch Gold was coming off a 4th place finish in the Preakness.
Trainer Bob Baffert was back in 1998 with Real Quiet, who was winless as a 3-year-old. He won the Kentucky Derby by 1/2 length and the Preakness by 2-1/4 lengths over Victory Gallop. In the Belmont, Victory Gallop caught Real Quiet at the wire by a nose.
In 1999 Charismatic ran in a claiming race only 3 months before the Kentucky Derby. He was a longshot winner by a neck in the Derby and won the Preakness by 1-1/2 lengths. After placing 9th in the Derby and 3rd in the Peter Pan, Lemon Drop Kid won the Belmont and Charismatic finished 3rd by 1-1/2 lengths but was injured in the stretch run and retired.
In 2002 War Emblem won the Kentucky Derby by 4 lengths, going wire to wire, then won the Preakness by 3/4 of a length. In the Belmont, he stumbled coming out of the gate, failed to get the lead, and could not run off the pace. Sarava, winner of the Sir Barton on the Preakness undercard, won at odds of 70-1. War Emblem was 8th, beaten 19-1/2 lengths.
In 2003, New York-bred gelding Funny Cide finished behind Peace Rules in the Louisiana Derby and second to Empire Maker in Wood Memorial, but beat these two favorites in the Kentucky Derby, winning by 1-3/4 lengths. In the Preakness, he won by 9 lengths, beating Peace Rules again. In the Belmont Stakes, Empire Maker won on a sloppy track and Funny Cide finished a well-beaten 3rd, 5 lengths behind.
In 2004 Smarty Jones took an unbeaten record into the Belmont. Smarty won the Kentucky Derby in the slop by 2-3/4 lengths and the Preakness by a record 11-1/2 lengths. In the Belmont, Smarty was weakened by a quick early pace allowing 36-1 longshot Birdstone (8th in the Derby) to pass him in the final strides and win by a length. Smarty Jones came out of the Belmont with injuries that forced his retirement.
In 2008 Big Brown took a lightly raced but undefeated record into the Triple Crown. He drew post 20 in the Kentucky Derby and won as the 2-1 favorite by 4-3/4 lengths. In the Preakness, he was the 1-5 favorite and won easily by 5-1/4 lengths. Big Brown joined Majestic Prince (1969), Triple Crown winner Seattle Slew (1977) and Smarty Jones (2004) as undefeated Derby and Preakness winners. Belmont Stakes day on June 7th was extremely hot at 97 degrees, and despite facing 9 rivals, all but 2 of which he had beaten previously, Big Brown's quest ended in an ignominious defeat. Da'Tara, as expected, broke on top and went right to the front. Big Brown, breaking from the rail, appeared to get distracted. He became rank just as he passed by the starter and stand. By this time, Big Brown was on the muscle and getting ranker by the second. Desormeaux was able to find another seam behind Tale of Ekati and abruptly steered Big Brown out, bumping with Anak Nakal. Big Brown finally was free, but was extremely wide as he headed down the backstretch. Meanwhile, 38-1 longshot Da'Tara had gotten away with a 48.30 half, as he led by a length over Tale of Ekati, who had moved up along the inside. With Big Brown in perfect striking position right behind in third through three-quarters in 1:12.90, passing the half-mile pole, Desormeaux began riding Big Brown and, shockingly, there was no response. The track had become deep and cuppy from the heat baking down on it, and it was obvious Big Brown was struggling over it. Da'Tara by now had opened a clear lead and kept extending it around the turn. When Denis of Cork ran right by Big Brown on his inside, it was the end of the favorite and the dream of a Triple Crown. Desormeaux, in melodramatic fashion, steered Big Brown abruptly toward the outside fence and began to ease him to a last place finish. Despite weeks of Dutrow boasting of greatness often seen as trashing any and all horses, even previous Triple Crown near misses, his horse was the first one seeking a Triple Crown to finish dead last. Da'Tara, who lost to Big Brown by 23-1/2 lengths in the Florida Derby and had only a maiden win to his credit, won by 5-1/4 lengths while earning a 99 Beyer Speed Figure, the lowest in the race since Beyer figures were first published in 1990. Because Big Brown came out of the race with no health issues, Desormeaux was widely criticized for his race tactics and blamed for the poor showing.