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Toronto Tempo vs. Chicago Sky prediction, pick for Wednesday 5/27/26

Toronto Tempo vs. Chicago Sky prediction, pick for Wednesday 5/27/26

Published:

By: Charlie Cummings

It’s early in the season, but the standings in the WNBA are awfully tight. 12 of the 15 teams in the league have either three or four wins. Two such teams are the Toronto Tempo and the Chicago Sky. Toronto wants to beat the odds and make a playoff push in its inaugural season, while Chicago wants to rebuild on the fly and get back into the postseason picture.

Tipoff is set for 8:10 p.m. ET. The Sky are 5.5-point home favorites with -205 moneyline odds on DraftKings Sportsbook. A Tempo upset is priced at +170. The game total is set at O/U 168.5 points.

Let’s get into a pick and prediction for this Tempo vs. Sky game.

Tempo vs. Sky Preview

The Tempo won’t be upset with their results so far. At 3-4, they’ve had some competitive losses along with quality wins. But back-to-back blowouts won’t sit well with this team, and head coach Sandy Brondello will demand more of her team.

Health is paramount here. Julie Allemand, Nyara Sabally, and Temi Fagbenle were all counted on to be significant contributors to this team. Those three have combined to miss 12 games so far. That places even more pressure on their star backcourt to deliver. Efficiency hasn’t been the name of the game for Brittney Sykes and Marina Mabrey—both are shooting 38% from the floor—but Sykes’ drives have been important to kick-starting the offensive flow, and Mabrey’s tough buckets have bailed them out of some tight spots. Once they get healthy, the hope is that they can improve on both ends of the court.

Chicago got off to a roaring start, fueled by an excellent defense and some timely bucket-getting. But the Rickea Jackson injury has taken the wind out of their sails. Since Jackson went down, the Sky have suffered back-to-back 10-point losses. With the defense taking a step back, it makes you wonder if those first four games were a mirage.

Still, important player development is happening. Kamilla Cardoso continues to take steps as a two-way paint anchor. Rookie Gabriela Jaquez has hit the ground running, bringing a necessary energy to their perimeter defense. The trade for Jacy Sheldon drew some ire, but she has been excellent in the early going. Even if the season ultimately ends in another playoff absence, there are good signs here.

Now we know these two teams a bit better. Who is going to come out the winner?

Tempo vs. Sky Pick, Best Bet

Things have looked rough under the hood for both of these teams. But the fact of the matter is, Toronto has the talent. Sykes and Mabrey have been inconsistent, but can take over games offensively. Kiki Rice has been excellent for a rookie. Without Rickea, Chicago is almost entirely reliant on a 35-year-old Skylar Diggins to create the majority of their offense. I’m still bearish on the Tempo as a whole, but they can simply out-talent the Sky.

Best Bet: Toronto Tempo Moneyline (+170)

Charlie Cummings is a Bay Area-born writer living in Denver. A basketball junkie, he specializes in NBA and WNBA content, but also dabbles in soccer, baseball, football and hockey. You can find him on Twitter @klaytheist11 where he’s posting through it on a daily basis.
Disclaimer

I am a promoter at DraftKings and am also an avid fan and user and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.