A look at 10 memorable editions of the Kentucky Derby, with the 150th running coming up on Saturday:

1933 (59th Derby)

Brokers Tip, ridden by Don Meade, came up the rail to challenge leader Head Play and jockey Herb Fisher. They ran side-by-side down the stretch, with Meade and Fisher grabbing arms and whipping each other in what became known as the “fighting finish.” The stewards declared Brokers Tip the winner by a nose; it was the only race he ever won. Meade and Fisher fought in the jockeys’ room afterward. Both were suspended 30 days. Fisher believed Brokers Tip should have been disqualified. Meade said years later that he couldn’t push Fisher away because he had hold of him, so he had to grab Fisher.

1915 (41st Derby)

Regret made a big splash as the first filly to win the Derby against male competition, propelling the race from a regional event into one of national and international interest. She led all the way under jockey Joe Notter and won by two lengths, snapping an 0-for-14 skid by fillies in the race. Regret, along with Genuine Risk (1980) and Winning Colors (1988), still are the only fillies to beat the boys. Only five have attempted the Derby since 1988. One of them — Eight Belles — was second in 2008 only to suffer a catastrophic breakdown beyond the finish line, stunning the crowd and television audience.

1948 (74th Derby)

On a sloppy track at Churchill Downs, Citation chased Coaltown throughout the 1 1/4-mile race before pulling away to a 3 1/2-length victory. A win bet paid $2.80; there was no place or show wagering because of the six-horse field. The colt and jockey Eddie Arcaro went on to win the Preakness and Belmont stakes to complete a Triple Crown sweep. It would be another 25 years before Secretariat accomplished the feat. Citation was the third of eight Derby winners for Calumet Farm, still the leading owner in Derby history.

1957 (83rd Derby)

The race featured three future Hall of Fame horses: Bold Ruler, Gallant Man and Round Table. None of them won but many consider their presence enough to comprise one of the greatest fields ever. One of the Derby’s most infamous moments occurred in the stretch: Bill Shoemaker, aboard Gallant Man, was challenging leader Iron Liege and Bill Hartack when Shoemaker misjudged the finish line. He stood in the saddle momentarily at the sixteenth-pole, long enough to ruin Gallant Man’s momentum and allow Iron Liege to a nose victory. It was the first of Hartack’s five Derby wins; Shoemaker won four. Gallant Man went on to win the Belmont.

1973 (99th Derby)

Secretariat was the first horse to win the Derby in under 2 minutes, in 1:59 2/5. He ran the last quarter-mile in 23 seconds, another record. Sham, the second-place finisher, also broke the old track record of 1:59 4/5. Secretariat rallied from 11th in the early going to win by 2 1/2 lengths under Ron Turcotte. In 2001, Monarchos came closest to beating Secretariat’s time, winning the Derby in 1:59.97. Secretariat went on to win the Preakness and earn an astounding 31-length victory in the Belmont. He became the ninth horse to sweep the Triple Crown, ending a 25-year drought. The big red colt’s times in all three races still stand.

1978 (104th Derby)

One of the sport’s greatest rivalries made the 1978 Derby memorable. Affirmed and Alydar had already met six times, with Affirmed winning four. With 18-year-old Steve Cauthen in the saddle, Affirmed beat Alydar by 1 1/2 lengths. The two horses went head-to-head in the Preakness and Belmont that year, with Affirmed sweeping the series to become racing’s third Triple Crown winner of the decade.

1990 (116th Derby)

Unbridled surged past rival Summer Squall to score a 3 1/2-length victory and paid $23.60 for a win bet. The chestnut colt was the first Derby runner for 92-year-old owner Frances Genter, who took over her husband’s stable after his death and won several major races. In the stands, trainer Carl Nafzger called the stretch run for Genter, whose failing eyesight kept her from seeing Unbridled thunder to the finish line. “He’s going to win! He’s going to win!” Nafzger said, his arms around her. “He’s a winner! Oh, Mrs. Genter, I love you!” He kissed her as millions watching on television were touched by Nafzger’s sweet affection. She died two years later. Nafzger won the 2007 Derby with Street Sense.

1997 (123rd Derby)

Silver Charm was the first of Hall of Fame trainer Bob Baffert’s record-tying six Derby winners. The colt took the lead with under a furlong to go and won by a head. Baffert had finished second the year before with Cavonnier. Silver Charm went on to win the Preakness, though his Triple Crown bid ended in defeat when he finished second in the Belmont. Silver Charm is the oldest living Derby winner at age 30.

2009 (135th Derby)

Last in the early going, 50-1 shot Mine That Bird moved up to 12th with a quarter-mile to go. Jockey Calvin Borel angled the small bay gelding back to the inside rail and shot him through a tight spot approaching the eighth pole. Mine That Bird accelerated through the slop to score a 6 3/4-length victory in the second-biggest upset at the time in Derby history. NBC race caller Tom Durkin was caught by surprise. “In a spectacular, spectacular upset, Mine That Bird has won the Kentucky Derby!” Durkin said. “An impossible result here!” The horse with the trainer and owners from New Mexico paid $103.20 to win. A movie was later made about their unlikely journey to triumph on the first Saturday in May.

2019 (146th Derby)

At 65-1 odds, Country House became the second-highest priced winner in Derby history in a highly unusual way. The colt and jockey Flavien Prat finished second to Maximum Security. Prat and Jon Court aboard Long Range Toddy filed objections to the result. It took 22 confusing minutes to sort out the final order of finish. The stewards said Maximum Security veered into the path of another horse, who was forced to check hard and in turn impeded another horse in a chain reaction. Maximum Security became the first horse in Derby history to be DQ’d for an on-track infraction. It was a bittersweet way for trainer Bill Mott and Prat to win their first Derby. The long-shot bettors went home happy as Country House paid $132.40 to win.

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