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Chicago Sky vs. New York Liberty prediction, pick for Saturday 8/29/26

Chicago Sky vs. New York Liberty prediction, pick for Saturday 8/29/26

Published:

By: Charlie Cummings

The FIBA World Cup break is right around the corner, and the WNBA regular season is drawing to a close. And the intensity has only risen. The Chicago Sky won’t make the postseason this year, but they’ve taken positive steps after a disastrous start and are looking to finish strong. In their way is a New York Liberty team fighting desperately to move up in the playoff standings. This one should be fun.

The Liberty enter as 8.5-point home favorites with -380 moneyline odds on DraftKings Sportsbook. The Sky are +300 underdogs, with the game total set at 178.5 points.

Let’s dive into a preview, prediction, and pick for this Sky-Liberty matchup.

Sky vs. Liberty Preview

This is the fourth and final regular-season meeting between these Eastern Conference rivals. So far, they’ve given us some entertaining basketball. New York won the first two matchups by one point apiece, but Chicago got their revenge two weeks ago with a 93-86 victory, throwing a significant wrench into New York’s postseason plans.

But Chicago’s chances of an upset got slimmer due to the injury report. Already struggling with the absence of Rickea Jackson and Skylar Diggins, they’ll have to get after it without Natasha Cloud and DiJonai Carrington. They’ll sorely miss their presence, especially against this Liberty team.

Now that she’s back to full health, Sabrina Ionescu is back to her old ways offensively, and that’s a big problem for the Sky. In their second matchup, the All-Star racked up 29 points on 8-of-11 shooting. Ionescu followed that up with 18 points and 12 assists in their most recent tangle. With Cloud and Carrington out, they’re going to be hard-pressed to keep her contained. This places a heavy burden on Rachel Banham, who will be asked to be the primary defender on New York’s star guard.

A major X-factor here is the play of Kamilla Cardoso. As Chicago’s frontcourt anchor, she’s going to be sorely tested against Jonquel Jones. That will force Cardoso to defend in space on one end and go to work against an elite defender on the other. That’s no easy task. But Cardoso has one thing on her side: size. With her immense build, she’s no stranger to getting physical, which has thrown Jones off in the past.

As always, Breanna Stewart is the matchup breaker here. Chicago, like most teams, has very little answer for her scoring prowess. If she gets to work in the midrange and starts unlocking things with her drives, the Sky will have a very hard time winning this one. Ionescu’s offensive skills are enough to get things in motion for the Liberty, and if Stewart provides her usual offense, it can turn ugly.

Sky vs. Liberty Pick, Best Bet

Frankly, it’s difficult to trust these Liberty right now. They’re all over the map, blowing out the Aces one day and losing to the Sky the next. Even though Chicago is dealing with injuries, I’ll take a stab at any half-competent team against New York.

Best Bet: Chicago Sky Moneyline (+300)

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.