Olympic viewing guide: Penny Oleksiak could make history

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Canada doubled its medal count on Day 4. Swimmer Kylie Masse kicked things off with a silver in the 100-metre backstroke last night before the women's softball team won its bronze game, Catherine Beauchemin-Pinard grabbed Canada's second judo bronze in as many days and weightlifter Maude Charron put an exclamation point on the day by snatching Canada's second gold medal of the Games. Women have won all eight of Canada's medals so far.

That trend could continue on Day 5, starting with one of Canada's most beloved Olympians trying to make history in the pool.

Here's your daily viewing guide focusing on Canada's best medal hopes, plus some tough news involving two of the Games' biggest international stars, Simone Biles and Naomi Osaka.

Penny Oleksiak could make history tonight

She just turned 21 last month, but Oleksiak already owns a share of the Canadian record for most medals won in the Summer Olympics. After racking up four as a 16-year-old in Rio, Oleksiak captured her fifth medal on Saturday night when she swam a blistering anchor leg to give the Canadian women's 4x100-metre freestyle relay team a silver. Rowing coxswain Lesley Thompson-Willie (1984-2012) and runner Phil Edwards (1928-36) are the only other Canadians to win five medals at the Summer Games.

If Oleksiak reaches the podium in the women's 200m freestyle tonight, she'll move into a tie with Cindy Klassen (speed skating) and Clara Hughes (speed skating and cycling) for the most medals by a Canadian in either the Summer or Winter Olympics (or, in Hughes's case, both). If she doesn't, Oleksiak will have another chance in the 100m freestyle (the event she won gold in at Rio 2016) and the 4x200 free (she helped Canada to bronze in Rio). The heats for those events are on Wednesday morning.

So, what are Oleksiak's chances tonight in the 200 free? She looked great in the heats, placing second overall to American Katie Ledecky, but not so great in last night's semifinals, finishing sixth as Australia's Ariarne Titmus posted the best time. The final is shaping up as another duel between Titmus and Ledecky, with the Aussie a clear favourite to win her second gold of the Games after edging Ledecky in the 400 freestyle. Also, this is not Oleksiak's best event. She finished second at the Canadian trials to 14-year-old Summer McIntosh, who didn't make it out of the semis last night.

But beyond Titmus, the podium might be more up for grabs than it appears. Ledecky has to compete in the 1,500m final a little over an hour later. That's her signature event, and this is the first time women have been allowed to swim it in the Olympics. Even though she's almost certainly going to win gold, you have to think she'll hold a little back for that historic race, which is the longest distance in swimming. The women's 200m freestyle final goes at 9:41 p.m. ET.

Canada has another shot at a swimming medal at 10:45 p.m. ET when Sydney Pickrem competes in the final of the women's 200m individual medley. She took bronze in this event at the most recent world championships, in 2019, and the Olympic field looks relatively balanced.

All of tonight's swimming races — including five finals — will be broadcast live on the CBC TV network starting at 9:30 p.m. ET. You can also stream them all live on CBC Gem, the CBC Olympics app and CBC Sports' Tokyo 2020 website.

WATCH | Kylie Masse makes magic in the water:

Other Canadian medal chances on Tuesday night/Wednesday morning

There's probably only one:

Rowing

A tropical storm caused two days' worth of races to be postponed, but rowers return to the water tonight at 7:10 p.m. ET. The first of six medal races goes at 8:18 p.m. ET, and there's a Canadian boat in it. The women's double sculls duo of Jessica Sevick and Gabrielle Smith isn't favoured to win a medal, but they've got a shot. Smith finished fourth with a different partner at the most recent world championships, in 2019.

Canada's top contenders for a rowing medal in Tokyo are Caileigh Filmer and Hillary Janssens, who took bronze in the women's pair event at the 2019 worlds. They compete in their semifinals tonight at 11:20 p.m. ET.

Other Canadians in important races tonight: Patrick Keane and Maxwell Lattimer in the men's lightweight double sculls semifinals at 10:10 p.m. ET, Jill Moffatt and Jennifer Casson in the women's lightweight double sculls semis at 10:50 p.m. ET, Kai Langerfeld and Conlin McCabe in the men's pair semis at 11:10 p.m. ET, and the women's eight in a repechage at 11:40 p.m. ET.

Some other interesting stuff you should know about

Simone Biles took herself out of the women's team final. The greatest gymnast of all time made the shocking decision after performing an uncharacteristically weak vault in the first rotation of today's event. The initial speculation was that she'd suffered an injury, but Biles later confirmed it had to do with her mental health. She admitted to "second-guessing" herself, which squares with what we saw in her tentative vault attempt, and said she thought it would be better to let her U.S. teammates take over for her. The defending champs ended up finishing second, behind whatever we're calling Russia. Biles's status for the individual competitions, which start with the all-around final on Thursday morning, is unclear. She said she'd "take it a day at a time." Biles is the first woman since 1992 to qualify for all six individual events at an Olympic Games. In 2016, she won three solo gold medals (in the all-around, vault and floor exercise) and a bronze in the balance beam after helping the U.S. to the team title. She took gold in all five of those events at the most recent world championships, in 2019. Read more about her pulling out of the team event, which was the biggest story of the Games today, here.

Naomi Osaka is out of the women's tennis event. The Japanese superstar has endured her own mental/emotional struggles of late. She walked away from the French Open in late May amid a dispute with organizers over her refusal to do press conferences, saying she needed a break for her mental health. Osaka then skipped Wimbledon before making what seemed like a triumphant return in Tokyo, where she was chosen to light the Olympic flame at last week's opening ceremony. But after beating overmatched opponents in the first two rounds, the world No. 2 was eliminated in straight sets today by 42nd-ranked Marketa Vondrousova of the Czech Republic. Read more about Osaka's disappointing exit here.

The Canadian women's soccer team will face Brazil in the quarter-finals. Today's 1-1 draw vs. Great Britain in their group-stage finale gave Canada second place in the group, behind the Brits. With Canada all but assured of advancing to the knockout stage before the match kicked off, coach Bev Priestman elected to rest 38-year-old captain Christine Sinclair. Underrated fullback Ashley Lawrence shined in Sinclair's absence, setting up Adriana Leon's goal with a blazing run down the wing and also doing some great work defensively. Read soccer analyst John Molinaro's full breakdown of today's match and his case for why Lawrence might be Canada's best player right now here. At the 2016 Olympics in Rio, Canada upset the host team 2-1 to win its second consecutive Olympic bronze medal. The rematch vs. Brazil is Friday at 4 a.m. ET. The winner faces either the top-ranked United States or the Netherlands in the semifinals.

Baseball starts tonight — and you might remember some of the guys in it. Canada didn't qualify for the tournament, but former Toronto Blue Jays fan favourite Jose Bautista is on the Dominican Republic's roster, which also includes ex-Jays Melky Cabrera and Emilio Bonifacio. A few other names baseball fans may recall from their major-league days: Ian Kinsler (Israel), Masahiro Tanaka (Japan) and Adrian Gonzalez (Mexico). The U.S. team includes Scott Kazmir, Todd Frazier and Eddy Alvarez, who played for the Marlins last year after winning a silver in short track speed skating at the 2014 Winter Olympics in Sochi. Read more about the memorable players in the Tokyo tournament here.

Photo of the day

Canadian divers Meaghan Benfeito and Caeli McKay came painfully close — literally — to making it a five-medal day for Canada. They missed the podium by just half a point in the women's 10m synchronized event and revealed later that McKay had competed on a badly injured foot. She tore ligaments during training three weeks ago, and doctors said she needed eight to 10 weeks to recover. But McKay simply refused to miss her first Olympic appearance. In the athletes' village, she pushed herself around on a scooter to take weight off the foot, and she fought through pain on all five dives last night. When it was over, Benfeito carried her wounded teammate out of their press conference. Read Devin Heroux's account of McKay's truly gritty performance here.

How to watch live events

They're being broadcast on TV on CBC, TSN and Sportsnet. Or choose exactly what you want to watch by live streaming on CBC Gem, the CBC Olympics app and CBC Sports' Tokyo 2020 website. Check out the full streaming schedule here.