Dallas Wings vs. Chicago Sky Prediction, Betting Pick, Latest WNBA Odds for Wednesday, May 20th
The Dallas Wings will look to shut down the Chicago Sky and their first place record on Wednesday night, coming to Chicago as a road favorite. Can Paige Bueckers and the Wings lock in defensively tonight? Let's take a look at this Wings vs. Sky prediction and best bet for Wednesday, May 20th.
OC Staff - May 20, 2026, 5:30 PM EDT
4 Minute ReadDallas Wings vs. Chicago Sky Prediction: Can Paige Bueckers, Wings Extinguish Sky's Hot Start in Chicago Tonight?
The Dallas Wings visit the Chicago Sky on Wednesday, May 20, at 9 p.m. ET on USA Network in a matchup between two teams coming off very different early-season statements. Dallas evened its record at 2-2 with a 92-69 win over Washington, while Chicago has opened 3-1 after a strong road-heavy start from a revamped roster.
The Sky have overachieved through the first week, but the market is already treating Dallas as the better side despite Chicago being at home. The best bet is under 169.5 total points, with Paige Bueckers and the Wings starting to look much more connected defensively after locking down a feisty Mystics team.
Dallas Wings vs. Chicago Sky Date, Time, and Where to Watch
- Date: Wednesday, May 20. 2026
- Time: 7:00 PM ET
- How to Watch: USA Network
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Dallas Wings vs. Chicago Sky Odds
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Dallas Wings vs. Chicago Sky Prediction
Dallas’ win over Washington was its most complete performance so far. Bueckers led the way with 18 points and seven assists, Arike Ogunbowale added 16, Jessica Shepard posted 12 points and 16 rebounds, and Azzi Fudd gave the Wings a lift off the bench. More importantly, Dallas held Washington to 69 points and forced enough mistakes to turn the game into a rout after halftime. That defensive effort is the version the Wings need to bring on the road.
Chicago’s 3-1 start deserves respect, especially after an offseason overhaul that brought in Skylar Diggins, Natasha Cloud, DiJonai Carrington, and Azurá Stevens. The Sky have played with toughness and energy, but this is still a new group that may be due for some offensive regression. Chicago has enough guard play to make this competitive, but it is not a team that should automatically pull Dallas into a track meet.
The matchup points toward a lower-scoring game because Dallas has the size and defensive activity to bother a mediocre Chicago offense. Shepard’s rebounding has stabilized the Wings inside, while Bueckers and Fudd give Dallas more length and pressure on the perimeter than the early-season numbers may suggest. If the Wings can again limit clean threes and keep Chicago out of easy transition looks, this total gets difficult to clear.
Dallas Wings vs. Chicago Sky Best Bet
- Pick: Under 169.5 Total Points (-110) Click here to get the best odds at DraftKings Sportsbook
Dallas just held Washington under 70, and the Wings are starting to show the defensive buy-in needed to support Bueckers’ offense. Chicago has been a good early story, but the Sky are likely to cool off in a tougher matchup against a Dallas team that can control pace, defend better, and keep this game under the number.
WNBA ODDS
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