The 2026 Winter Olympics in Milano Cortina delivered thrilling moments in alpine skiing, where unexpected outcomes led to enormous betting payouts. Held from February 6 to 22 across venues like Bormio and Cortina d'Ampezzo, the games featured intense competitions in downhill, super-G, slalom, and more.
While favorites often faltered due to treacherous conditions and injuries, underdogs rose to claim gold, rewarding bold bettors with life-changing sums at Upspins. This article explores the largest reported wins, focusing on the athletes, events, and dramatic turns that fueled them.
Underdog Swiss Sensation Shocks in Mens Downhill
One of the biggest payouts came from a wager on Franjo von Allmen in the men's downhill event on February 7 at the Stelvio Ski Centre in Bormio. The 25-year-old Swiss skier, relatively new to the elite scene, entered with odds around 3.5 to 1 after strong but inconsistent World Cup showings. Pre-race favorites like Marco Odermatt dominated predictions due to his dominant season, but von Allmen capitalized on perfect conditions and flawless technique.
Clocking 1:51.61, von Allmen edged out Italy’s Giovanni Franzoni by 0.20 seconds for gold, with Dominik Paris taking bronze at +0.50. His victory marked Switzerland's first downhill Olympic gold since 2014, showcasing aggressive line choices on the steep, icy piste. A reported bettor from Europe placed 5000 euros on von Allmen pre-event, netting over 17500 euros in payout. This win highlighted von Allmen's breakout status, as he later added super-G and team combined golds, but the downhill upset sparked the largest single-event windfall in alpine betting for the games.
Italian Comeback Queen Defies Odds in Women's Super-G
Federica Brignone's triumph in the women's super-G on February 12 at Cortina d'Ampezzo Tofane course produced another massive payout amid chaotic conditions. The 35-year-old Italian veteran, returning from multiple leg fractures and a torn ACL suffered in 2025, faced long odds of 10 to 1 or higher. Foggy flat light and a treacherous track caused over a dozen crashes, including favorites like Sofia Goggia and Ester Ledecka, turning the race into a survival test.
Brignone, starting mid-pack, navigated the technical sections with precision, posting a time that held as 17 of 42 competitors failed to finish. She claimed gold ahead of Lara Gut-Behrami in silver and Cornelia Huetter in bronze. Her emotional victory on home soil, just weeks after resuming training, symbolized resilience. One anonymous punter reportedly staked 2000 dollars on Brignone, collecting around 20000 dollars. This event underscored the unpredictability of super-G, blending speed and turns, and rewarded those betting on local knowledge and experience over form.
Norwegian Meltdown Hands Swiss Gold in Mens Slalom
The men's slalom on February 16 at Bormio provided a dramatic upset payout when Loic Meillard seized gold after favorite Atle Lie McGrath's collapse. McGrath, a Norwegian technical specialist with multiple World Cup wins, led by 0.59 seconds after the first run but straddled a gate in the second amid blizzard conditions, finishing out of medals. Meillard, a consistent Swiss performer with odds at 5.5 to 1, delivered steady runs to win by a narrow margin.
His time edged out Clement Noel of France in silver and Henrik Kristoffersen of Norway in bronze. Meillard's victory was Switzerland's second slalom gold in recent Olympics, thriving on the gates tight setup and variable snow. A bettor from Asia allegedly wagered 3000 pounds on Meillard, yielding over 16500 pounds.
American Icon Rebounds for Slalom Glory Amid High Stakes
Mikaela Shiffrin's gold in the women's slalom on February 18 at Cortina capped the alpine events with a substantial betting win for her supporters. The 30-year-old American, despite recent inconsistencies, held favorite status but faced skepticism after early-season struggles, with odds dipping to 2.5 to 1. She dominated both runs with a combined 1:39.10, outpacing Camille Rast of Switzerland by 1.50 seconds and Anna Swenn Larsson of Sweden in bronze.
Shiffrin's performance reaffirmed her GOAT status, securing her second Olympic slalom title 12 years apart on a course favoring her technical prowess. A group of fans reportedly pooled 10000 dollars on her victory, splitting a payout exceeding 25000 dollars. This event closed the games on a high note, blending legacy with high-reward betting.