Masse, Ruck qualify for 200m backstroke semis after battling Aussie star McKeown

Kylie Masse might need star Australian swimmer Kaylee McKeown to be at less than top form if she is to capture her first Olympic gold medal in the 200-metre backstroke.

First, the Canadian record holder will need to make it through Friday's semifinals (Thursday at 10:35 p.m. ET in Canada) after placing in a second-place tie with American Rhyan White, behind top qualifier McKeown in Tokyo.

McKeown sat second behind Taylor Ruck of Kelowna, B.C., and ahead of third-place Masse late in Thursday's heat race before taking control over the final 50 metres to post a winning time of two minutes 8.18 seconds at the Tokyo Aquatics Centre.

Masse was 5-100ths of a second behind in second place, followed by Ruck, who was third and qualified sixth of 16 swimmers in 2:08.87.

"Just doing what I need to do to get the first round and I felt pretty smooth," Masse told Swimming Canada. "I'll look back at the race and see what I can improve upon and get the best rest and recovery for the next step."

WATCH | Canada's Masse, Ruck advance to backstroke semifinals:

Kylie Masse has learned to truly appreciate quality time with her family

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On Tuesday, the 25-year-old Masse narrowly missed gold in the women's 100 backstroke, earning silver after leading midway in a race won in Olympic record time by the 20-year-old McKeown, her first gold at a Summer Games.

If Masse advances to Friday's final at 9:37 p.m. ET, she'll be looking to add to her international haul in the event, having captured bronze at the 2019 world championships and Commonwealth Games gold a year earlier.

Ruck, who missed qualifying for the 100 backstroke final by 37-100ths of a second, is hoping for a chance to medal in the 200 after winning bronze in 100 and 200 relay competitions at the 2016 Rio Olympics.

"I'm pretty pleased with the race, this meet has been more downs than ups I'm just trying to keep my head in this last stretch of the Games," said Ruck, a member of Canada's 4x100 freestyle silver medal-winning team in Tokyo who didn't race in the final.

WATCH | Masse leans on family during pandemic:

Canada's Liendo into men's butterfly semis

Joshua Liendo of Markham, Ont., was third in his 100 butterfly heat and qualified ninth in 51.52 seconds for the semifinals on Thursday at 9:30 p.m. ET.

"My turn wasn't the way I wanted," said Liendo, third in his heat. "I shortened up and didn't get around too fast [but] if I fix that, that's a lot of time [saved]. I'm [in the semifinals] and that's all that matters right now."

The 18-year-old first-time Olympian set a national record of 51.40 on the opening day of Canadian trials in June before winning the competition in 51.72 at Toronto's Pan Am Sport Centre.

WATCH | Liendo nearly lowers his Canadian mark in butterfly heats:

Earlier this week, Liendo failed to qualify for the men's 100 freestyle final after helping the Canadian relay team set a national record in the 100 free.

Swimming Canada's 2019 male junior swimmer of the year is also expected to compete in the men's 50 free heats, which begin Friday at 6 a.m. ET.

Dressel sets Olympic mark in butterfly heats

American sensation Caeleb Dressel set an Olympic record of 50.39 to finish tops in Thursday's qualifying, mere hours after the 24-year-old won the 100 freestyle final over defending champion Kyle Chalmers for his first individual Summer Games gold medal.

The first three gold medals of Dressel's career were all in the relays — two in Rio and another in the 4x100 free relay earlier in these Games.

The Florida native is 2-for-2 in medal attempts so far in Tokyo, and should he win all seven of his events, Dressel would join select company in fellow Americans Mark Spitz, Matt Biondi and Michael Phelps, who holds the single-Games record of eight.

McIntosh lowers 800m free PB by over 4 seconds

Summer McIntosh of Etobicoke, Ont., took more than four seconds off her personal best in the women's 800-metre freestyle heats on Thursday and set a Canadian age-group record, but failed to qualify for her third swimming final in Tokyo.

The 14-year-old led start-to-finish in her heat, clocking 8:25.04 to shatter her previous best of 8:29.48 on June 21 at Olympic trials.

McIntosh also set a national age-group mark in the women's 200 free relay final on Thursday, swimming the first leg in 1:55.74. The foursome of Kayla Sanchez, Rebecca Smith, Penny Oleksiak and McIntosh placed fourth in a national record of 7:43.77.

"'I'm not super over the moon about my result," McIntosh said of the 800 race. "The race went pretty well but I know I have more room to improve with many aspects like my turns and just overall a bit faster with my pace. But I'm still pretty happy with how it went after a quick turnaround from this morning."

In the women's 400 free, McIntosh's first Olympic final, she finished fourth and lowered her Canadian record time to 4:02.42 after going 4:02.72 in qualifying to break Brittany MacLean's 4:03.43 national record from the 2016 Rio Olympics.

In the 4x100 mixed medley relay — which is new to Olympic competition — Canada's Javier Acevedo, Rebecca Smith, Gabe Mastromatteo and Katerine Savard were 13th overall in 3:46.54 and nearly three seconds behind Israel, the eighth and final qualifying team for the final.

"I think we did a pretty good job," said Savard, a three-time Olympian. "We wanted to have fun, do our best but it wasn't enough to make the final. Still, we should be happy about ourselves."

Bird-flipping Condorelli now competing for Italy

Former Canadian swimmer Santo Condorelli also competed in the men's butterfly on Thursday after becoming eligible to represent Italy internationally in November 2018.

The 26-year-old, who finished in 52.32 and didn't advance to the semifinal, placed fourth for Canada in the men's 100 freestyle at the 2016 Games. He also had a stint with the U.S. swim team.

The self-proclaimed "most international of international swimmers" also made headlines for his notorious pre-race middle-finger flashing. When he was eight years old, Condorelli was frustrated racing against, and getting beat by, older swimmers, so his father and coach, Joseph, came up with the idea for the son to flip dad the bird before each race.