5 of the biggest sports parlay wins of all time

​​Marco Piemonte earned the moniker "Million Dollar Marco" by winning multiple $1 million bets in a year. His crowning achievement involved three Memorial Day baseball games and an NBA playoff tilt the next night: the Washington Nationals (+110) to top Atlanta, the Colorado Rockies (+100) to beat the Cleveland Guardians, the San Francisco Giants (-135) to vanquish the Philadelphia Phillies, and the Minnesota Timberwolves (+120) to overcome the Dallas Mavericks.

The Nationals cruised to an 8-4 victory, and the Giants won by the same score. And while the Guardians led 4-1 early, the Rockies scored six runs in the fourth inning of an 8-6 comeback triumph, ending Cleveland's nine-game winning streak by getting to one of its worst starting pitchers, Xzavion Curry.

That left the leg with the longest odds. The Wolves were trailing the Mavericks 3-0 in the Western Conference Finals, but they finished a game strong, with Karl-Anthony Towns and Anthony Edwards holding off the homesteading Mavericks, 105-100. Dallas never led by more than four points, and Piemonte's biggest parlay payout was assured.

Six months before that bonanza, Piemonte won an even more improbable wager: a 13-leg parlay of nine football games and four NBA contests. He wagered $40,000 to come away with nearly $1.6 million.

Rolling so many bets into one multiplies the risk, of course, but Piemonte mitigated much of that by gambling on eight alternate point spreads, such as the Las Vegas Raiders +25.5 at -572 odds. The other legs were money lines, and he had to sweat out the Denver Broncos (-130)—who needed a pair of second-half takeaways to get back in their game against the Minnesota Vikings and scored a late touchdown in a 21-20 victory—as well as Maryland's threat to shock Michigan (-1200), with the Wolverines winning 31-24.

The Los Angeles Clippers also needed a last-minute comeback in a close game to top the Houston Rockets, but that was the fourth leg, and thus the stakes hadn't fully come into focus.

This jackpot came with a caveat, too. Piemonte increased his potential earnings—but also risked cutting into the $1.6 million at stake—by hedging $500,000 on the last leg. If Kansas City had beaten the Philadelphia Eagles, who were getting 10 points at -408 odds in the parlay, by 7-10 points, he would've banked another $1 million. Kansas City led 17-7 at halftime but lost 21-17.

This story of a horse racing bettor who struck it rich is as good as it gets.

Steve Whiteley, a social gambler who was at the track with friends because he had free tickets from a promotion, as The Guardian reported in 2011, couldn't afford the £32 slip he filled out in a rollover Jackpot contest. Instead of picking two horses in each of the six races, he had to pick just one in each race. That £2 flier mushroomed into a £1.5 million windfall.

Whiteley's winning picks are best described as random, and he had a couple of nail-biters. In the fourth race, Mr. Bennett won after two favorites fell and a third horse lost its rider at the last jump.

In the final race, Lupita, in her 29th run, won for the first time, getting by Only Hope in the last furlong. Jessica Lodge, the jockey, had also not won in all 19 of her starts. Whiteley's payout nearly tripled the 45-year-old Jackpot's previous high.

The Houston Texans exceeded expectations last season, and their Week 10 victory at the AFC heavyweight Cincinnati Bengals was arguably their best showing. For one bettor, it paid off in a big way.

They wagered $500,000 to win $5.5 million on a four-leg parlay in which the game's point total had to exceed 45.5, the Texans had to win, and Houston running back Devin Singletary had to rush for more than 51.5 yards and score a touchdown.

The picks were right on the money. Singletary had reached 59 rushing yards on just eight carries by early in the second quarter and finished with 150. He scored from six yards out midway through the third quarter to help the Texans to a 20-7 lead—and spark a scoring spree that pushed the total to 44 points early in the fourth.

The Bengals' Joe Mixon scored with 3:18 to play to clear 45.5—and help pull Cincinnati within three. It tied the game at 27 with 1:33 to go, but C.J. Stroud, Houston's rookie quarterback, engineered a six-play, 55-yard drive that ended with Matt Ammendola's 38-yard game-winning field goal as time expired.

Back to the parlay king, Marco Piemonte.

This combination featured two college football and four NFL bets in September 2022. He wagered $65,000 on Minnesota (-145) to beat Michigan State, the Indianapolis Colts (+200) to beat Kansas City, the Jacksonville Jaguars (+140) to beat the Los Angeles Chargers, plus Arkansas (+2), the Green Bay Packers (+1.5), and the Denver Broncos (+1.5) to cover point spreads.

That Saturday, the visiting Golden Gophers crushed the Spartans 34-7. The Razorbacks, playing Texas A&M, came up short 23-21—a push that voided that leg, slicing the potential payout from $5.7 million to $3 million.

Sunday started right with the Colts' 20-17 upset, which included Kansas City fumbling a punt return, missing a field goal, and throwing a last-second interception. After the Jaguars' 38-10 rout, the Packers scored two touchdowns on their first two drives at the Tampa Bay Buccaneers and held on, winning 14-12.

That set up the Broncos' Sunday Night Football game versus the San Francisco 49ers. Under first-year head coach Nathaniel Hackett, Denver finished 5-12 that season. But, before the wheels came off, the Broncos posted a defensive gem, recording three sacks, three takeaways, and a safety in the second half to edge the 49ers 11-10.

Data reporting by Karim Noorani. Story editing by Shanna Kelly. Additional editing by Kelly Glass. Copy editing by Robert Wickwire. Photo selection by Clarese Moller.