Night 5 at the 2024 U.S. Olympic Swimming Team Trials presented by Lilly featured the busiest evening of racing yet, and the first big upset of the Trials.

Chris Guiliano out-sprinted big-name rivals Caeleb Dressel and Jack Alexy to win the men's 100m freestyle, instantly becoming a rising star in his own right.

Kate Douglass flexed her world-class versatility, competing in (and winning) two polar-opposite events within an hour and a half.

Katie Ledecky showed why she remains the undisputed queen of distance swimming, crushing the field in the 1500m freestyle to the thrill of the Lucas Oil Stadium crowd.

See below for event-by-event recaps, highlights and results from Indy.

Kate Douglass was the class of a stacked first final of the night, winning the women's 100m free in 52.56 seconds to officially lock in her spot at the Paris Olympics. She not only booked herself a lane for the same event in Paris, but also a key spot on the U.S. 4x100m freestyle relay.

"I really just wanted to try to get back down to 52.5 (seconds) in that race and I'm really happy I did, and I'm really excited to be on this relay in Paris," Douglass said on NBC after the race.

Douglass will be joined on the relay squad by Torri Huske, Gretchen Walsh, and Simone Manuel, who assured herself a spot at her third career Olympic Games.

Huske, the only other swimmer besides Douglass to crack 53 seconds, will also likely swim alongside Douglass in the individual event.

FINAL RESULTS:
1) *Kate Douglass | 52.56
2) *Torri Huske | 52.93
3) *Gretchen Walsh | 53.13
4) *Simone Manuel | 53.25
5) **Abbey Weitzeil | 53.70
6) **Catie Deloof | 53.86
6) **Erika Connolly | 53.86
8) Beata Nelson | 54.00
*Olympic place guaranteed
**Olympic place possible

Virginia native Thomas Heilman, 17, is a first-time Olympian.

So too, in all likelihood, is 22-year-old Californian Luca Urlando, finally healthy after multiple injuries slowed his rapid ascent as one of America's best butterfly swimmers.

Heilman and Urlando emerged from a wide-open men's 200m fly final, touching in 1:54.50 and 1:55.08, respectively.

Both will attempt to become the first Americans to win an Olympic medal in this event since Michael Phelps did so at the 2016 Rio Olympics, his final Games.

FINAL RESULTS:
1) *Thomas Heilman | 1:54.50
2) **Luca Urlando | 1:55.08
3) Mason Laur | 1:55.37
4) Dare Rose | 1:55.70
5) Colby Mefford | 1:56.43
6) Jack Dahlgren | 1:56.63
7) Trenton Julian | 1:57.07
8) Zach Harting | 1:57.69
*Olympic place guaranteed
**Olympic place likely

One day after setting a world record in the women's 100m backstroke, Regan Smith showed why she's a medal contender in multiple events for Paris. Smith wrapped up the women's 200m fly semifinals with the top time of 2:04.91, best of the session by over a full second.

Meanwhile, it's been a pretty successful Father's Day week for Nick Shackell so far. On Saturday, the former Great Britain Olympic swimmer watched his son, Aaron, secure his first Olympic team spot.

Daughter Alex is well on her way to adding another Olympian to the family. The 17-year-old won the second semifinal in 2:06.10, second only to Smith across both heats. She'll have a middle lane for the final.

ADVANCING TO FINAL:
1) Regan Smith | 2:04.91
2) Alex Shackell | 2:06.10
3) Emma Sticklen | 2:07.44
4) Dakota Luther | 2:08.36
5) Lindsay Looney | 2:08.60
6) Tess Howley | 2:08.79
7) Lucy Bell | 2:08.90
8) Charlotte Hook | 2:09.50

It was always about the time and the margin of victory for Katie Ledecky in the women's 1500m free. In the end, those figures were 15:37.48 (the fastest time in the world in 2024) and 20 seconds.

Ledecky, the holder of the 18-fastest times in the event's history, did nothing but reaffirm her status as the overwhelming gold-medal favorite for Paris.

"I would have loved to have been a little faster, but I'll take it and I'll be better in a few weeks [at the Olympics]," Ledecky said.

The only other swimmer under 16 minutes in the final was Katie Grimes, who adds the mile to her growing list of Paris events that also includes the 400m IM and the 10K open water swim.

Grimes qualified alongside Ledecky in the 800m free at the 2021 Trials, where they coined themselves "Katie Squared."

FINAL RESULTS:
1) *Katie Ledecky | 15:37.35
2) **Katie Grimes | 15:57.77
3) Ashley Twichell | 16:08.07
4) Kate Hurst | 16:09.77
5) Aurora Roghair | 16:09.79
6) Rachel Stege | 16:10.03
7) Erica Sullivan | 16:29.88
8) Mariah Denigan | 16:34.19
*Olympic place guaranteed
**Olympic place possible

Just 150 meters into the second men's 200m backstroke semifinal, it would have appeared to the untrained eye that four-time Olympic gold medalist Ryan Murphy was in trouble. Turns out, he was just getting started.

Murphy turned at the three-quarter mark in third place, but surged to the lead before breaking the surface from his world-class underwaters. He finished in 1:55.69, ahead of Jack Aikins.

However, Cal freshman Keaton Jones, winner of the first semifinal, set the top overall time in 1:55.49 and will swim in the final aiming to make his first Olympic team.

ADVANCING TO FINAL:
1) Keaton Jones | 1:55.49
2) Ryan Murphy | 1:55.69
3) Jack Aikins | 1:55.95
4) Tommy Janton | 1:56.87
5) Daniel Diehl | 1:57.29
6) Jay Litherland | 1:57.59
7) Hunter Tapp | 1:57.79
8) Caleb Maldari | 1:57.99

Swimming her second event of the evening and clearly exhausted after touching the wall, Kate Douglass still managed to post the top time of the 200m breaststroke semifinals in 2:21.23, cementing her as the favorite in the final.

The real drama came in the first semi, where Lilly King charged late to overtake Alex Walsh to the excitement of the Indianapolis crowd.

The two Olympic medalists finished less than four-tenths apart, and will likely duel for the presumptive second Olympic team spot in the final, behind Douglass.

ADVANCING TO FINAL:
1) Kate Douglass | 2:21.23
2) Lilly King | 2:22.45
3) Alex Walsh | 2:22.81
4) Ella Nelson | 2:23.84
5) Kaelyn Gridley | 2:25.82
6) Anna Keating | 2:27.60
7) Raya Mellott | 2:28.61
8) Isabelle Odgers | 2:29.03

Matt Fallon entered the 200m breaststroke final at the 2021 Trials as the top qualifier, then experienced disaster in the final when he finished eighth.

He entered in the top spot once again at Trials, and this time, he got the job done with emphasis. Now though, Fallon isn't just a U.S. Olympic team member for the first time, he's also an American record holder.

Fallon finished in 2:06.54 for a new all-time best American mark and the top time in the world in 2024.

"I could be dreaming right now and I wouldn't even know it," Fallon said afterward.

Josh Matheny will likely join Fallon in Paris as runner-up in the final.

FINAL RESULTS:
1) *Matt Fallon | 2:06.54 (AR)
2) **Josh Matheny | 2:08.86
3) A.J. Pouch  | 2:09.05
4)  Will Licon | 2:09.38
5) Daniel Roy | 2:09.44
6) Nic Fink | 2:09.56
7) Jake Foster | 2:09.64
8) Josh Bey | 2:11.66
*Olympic place guaranteed
**Olympic place possible

In what was billed as a showdown between American stars Caeleb Dressel and Jack Alexy in the men's 100m freestyle, it was Chris Guiliano who posted the best time in each round, including winning the final.

The Notre Dame swimmer touched in 47.38 seconds to earn his first Olympic team spot. Alexy took second place, nine-hundredths later. Dressel was third, another six tenths behind.

Therefore, Dressel won't get the chance to defend his 100m freestyle gold medal in Paris. However, he still confirmed his place on Team USA on the 4x100m relay team alongside Guiliano, Alexy and Hunter Armstrong.

After the race, Dressel indicated that the quartet will aim to break the world record in Paris.

FINAL RESULTS:
1) *Chris Guiliano | 47.38
2) *Jack Alexy | 47.47
3) *Caeleb Dressel  | 47.53
4)  *Hunter Armstrong | 47.78
5) **Ryan Held | 47.82
6) **Matt King | 47.94
7) Destin Lasco | 48.14
8) Macguire McDuff | 48.64
*Olympic place guaranteed
**Olympic place possible