The Winter Olympics debuted in 1924, and a full century later, athletes are still making history.

Whether it’s through their age, medal tally or times, Olympians are sure to make records fall during the 2026 Milan Cortina Games. Here’s a look at some of the record-breaking performances these Winter Olympics could provide.

Klaebo Could Add to Legacy With Historic Medal Haul

At 29 years old and entering his third Olympics, Johannes Hosflot Klaebo has already established himself as a cross-country skiing legend, but this season could catapult the Norwegian’s stardom to whole new levels.

Klaebo already has seven Olympic medals, including five golds, across his last-two appearances. He could nearly double that haul at the Milan Cortina Games, as he is a gold-medal contender (or outright favorite) in six events. It wouldn’t be unprecedented for him either — he swept all six events he entered at the 2025 World Championships.

Winning four gold medals would make Klaebo the winningest Winter Olympian of all-time, and winning five would put him on a list with Michael Phelps (23 gold medals) as the only athletes (summer or winter) to have 10 or more gold medals. If Klaebo earns six medals of any color, he would be the first Winter Olympian to do so at a single Games.

Klaebo is also just three wins shy of his 100th World Cup victory, a milestone that he’s likely to hit ahead of Milan Cortina 2026.

Vonn Returns, Looks to Become Alpine Skiing’s Oldest Medalist

Since coming out of a five-year retirement, U.S. Alpine skiing star Lindsey Vonn has proven herself to still be a medal contender. In March, she capped off her comeback season with a 2nd-place finish in a super-G race, making her the oldest woman to ever finish on the podium at an Alpine skiing World Cup event.

If she can finish on the podium in Cortina, the 41-year-old Vonn would become the sport’s oldest Olympic medalist.

Gu Could Continue Ascent Up Freestyle Skiing’s Medal Table

Four years ago, Eileen Gu became the first athlete to win three freestyle skiing medals at a single Winter Olympics. She’s one of the few athletes — freeskier or snowboarder, man or woman — who competes in all three park and pipe events (halfpipe, slopestyle, big air), and she does so at a high level.

Although Gu, who was born in the U.S. and competes for China, has focused primarily on halfpipe during this Olympic quad — and hasn’t competed in big air at all — she’ll be considered a medal contender for all three events. No athlete has won more than three freestyle skiing medals for their whole career. If Gu repeats that feat in Livigno, she’s guaranteed to have sole possession of the sport’s all-time lead.

Friedrich Looks to Become Bobsled's Winningest Olympian

Francesco Friedrich has consistently piloted Germany to Olympic and world titles in two-man and four-man bobsled. He swept both events at each of the last two Winter Olympics, and his four gold medals are tied for most in the sport.

A fifth gold medal would break the tie and put Friedrich atop his sport’s all-time leaderboard. It’s hard to bet against the 35-year-old, as he’s swept both events at each of the last two world championships.

Team USA’s Kaillie Humphries (3 gold medals) is within reach of that record as well.

Which Snowboarder Will Be the First to Three-Peat?

No snowboarder, not even the great Shaun White, has ever won the same event at three consecutive Olympics. At the Milan Cortina Games, three women could pull off the three-peat.

American Chloe Kim, the heavy favorite in women’s halfpipe, is the strongest bet to do so, but her opportunity comes last.

The first woman is Czechia’s Ester Ledecka, who will forego Alpine skiing’s downhill event, which is happening at a venue several hours away on the same day, in favor of a shot at history in snowboarding’s parallel giant slalom event. Ledecka, the first athlete to win gold in two different sports at the same Olympics, earned downhill bronze at last season’s world championships. In addition to being the two-time defending Olympic champion, she’s also the reigning world champion in PGS.

Anna Gasser, who won back-to-back big air titles in PyeongChang and Beijing, will be the second snowboarder with a shot at a three-peat.

Shiffrin Attempts to Build on Olympic Legacy

Mikaela Shiffrin has more World Cup victories than any Alpine skier in history, but she’s still working her way up the all-time Olympic medal table.

Entering these Games, Shiffrin’s two gold medals are currently tied for most all time among U.S. Alpine skiers. A gold medal in Cortina would make her the country’s winningest Alpine skier in Olympic history. (Lindsey Vonn, who has one gold medal, is also within that distance of that record.)

Two gold medals could potentially move Shiffrin into a tie atop the all-time leaderboard for all athletes (and a third could potentially give her the record), but that also depends on the results of other competitions at these Games.

As of now, Shiffrin plans to race slalom and giant slalom at the Milan Cortina Olympics, and is likely to compete in the team combined event. Super-G remains a possible addition to her schedule.

More Potential History at the Winter Olympics

• In what she has said will be her final Olympics, Hilary Knight is set to become the first U.S. hockey player to compete at five Winter Games. A fifth medal, of any color, would tie the record for most all-time by a hockey player.
• The U.S. trio of Emery Lehman, Ethan Cepuran and Casey Dawson holds the world record (set in 2024) in speed skating’s team pursuit event and won last year's world title. Could they potentially improve on their record mark at these Games?
• Entering these Games, Austria’s Claudia Riegler (44 years old) is the oldest snowboarder to ever compete at the Olympics. That record will surely fall, but it could stay with Riegler, now 52, who didn’t compete in Beijing but is still active on the World Cup circuit.