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Chicago Sky vs. Dallas Wings prediction, pick for Saturday 6/20/26

Chicago Sky vs. Dallas Wings prediction, pick for Saturday 6/20/26

Published:

By: Charlie Cummings

The Wings are rocketing into the playoff picture, while the Sky struggle to put things together in the post-Angel Reese era. Can Dallas continue marching toward its first postseason in three years? Or will Chicago be able to play the spoiler?

Tipoff is set for 8 p.m. ET. The Wings are 9.5-point home favorites with -425 moneyline odds on DraftKings Sportsbook. A Sky upset is priced at +330 with the game total set at O/U 170.5 points.

Let’s get into a pick and prediction for this Sky-Wings game.

Sky vs. Wings Preview

Very little is going right for the Chicago Sky these days. After scrapping to a 3-2 start, they’ve lost eight of their last nine games, looking like the lottery team we all expected them to be. Their defense has fallen off a cliff since a strong start, while the offense remains quite bad. It’s going to be a long, long season in the Windy City, and watching Angel Reese thrive in Atlanta isn’t making things easier.

But it hasn’t been all bad. Jacy Sheldon has been a positive addition to their backcourt, providing strong defense, solid drives, and passable floor spacing. Gabriela Jaquez has hit the ground running as a rookie and has the look of a quality wing starter for years to come. Kamilla Cardoso may not be a foundational piece, but she remains a strong frontcourt presence. Natasha Cloud has been a great veteran addition and should net a good price as a deadline rental if the Sky opt for that path. It’s going to have to get a lot worse before it gets better, but there are positive signs here.

For Dallas, it’s all heading up. Paige Bueckers continues to take steps as the franchise superstar and looks like a legitimate MVP candidate. Jessica Shepard has scaled up beautifully this year, becoming a nightly double-double threat and earning serious All-Star hype. Head coach Jose Fernandez has figured out how to make Arike Ogunbowale lineups work. And, despite the endless Olivia Miles comparisons, Azzi Fudd continues to ball out defensively and is an extremely efficient play finisher on offense.

It’s not all about the stars for Dallas. Aziaha James has given them a lot of energy with her floor-slapping, give-me-your-best-scorer mentality. Awak Kuier is finally stepping into an offensive role while remaining a defensive force. Sug Sutton has given them a shot in the arm after signing. It’s a deep team with high-end talent to make some noise, and they’re top-five in both offensive and defensive ratings. Don’t be surprised if this team can win a round or two in the postseason.

If the Sky want to pull the upset, Cardoso has to be a monster in the paint. They need Sheldon to be active on her drives and make an impact on the perimeter against Bueckers and Fudd. Otherwise, it’s going to be a long night; Skylar Diggins isn’t enough by herself to break this strong Wings defense, and few people have had an answer for Paige. That talent threatens to overwhelm Chicago if they’re not careful.

Now we know what to make of these two teams. Who is going to take home the win?

Sky vs. Wings Pick, Best Bet

I’m surprised this spread isn’t a lot higher. Dallas isn’t an inner-circle contender just yet, but they certainly have the look of a playoff team, and the underlying numbers love them. Quality depth with high-end superstar talent is a tried-and-true formula. Chicago has some nice things going, but they’re racking up loss after loss for a reason: they don’t have anything to lean on consistently. I expect Dallas to handle business in this one.

Best Bet: Dallas Wings -9.5 (-110)

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.