May 20, 2026
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Read Article Wings vs. Sky prediction: Paige Bueckers projected to score 20 points in Wednesday's WNBA game [5/20/2026]
Updated: | First published:
Written by Dave Garofolo, Content Producer
Get Dallas Wings vs Chicago Sky predictions for WNBA Wednesday.
The Chicago Sky will square off with the Dallas Wings in WNBA action at Wintrust Arena on Wednesday, starting at 9:00 PM ET.
Based on the latest simulation results, Dimers' proven WNBA model predicts the Wings as the most likely winner of the Wings vs. Sky game.
The Sky, led by Skylar Diggins-Smith, Kamilla Cardoso and Natasha Cloud, are set to take on the Wings, featuring Paige Bueckers, Arike Ogunbowale and Jessica Shepard.
Bueckers, the young phenom making headlines with the Wings, is expected to shine with a projected 20 points and 1 threes.
This article offers an expanded analysis of Wednesday's matchup, including best bets and player prop picks.
Wings vs. Sky prediction: Who will win and cover?
Using innovative machine learning and statistical analysis, we have simulated the outcome of Wednesday's WNBA matchup between the Wings and Sky, forming part of our WNBA predictions coverage.
Our famous predictive model currently gives the Wings a 70% chance of defeating the Sky.
According to our model, the Wings (-2.5) have a 61% chance of covering the spread, while the over/under total of 169.5 points has a 58% chance of staying under.
Wings vs. Sky odds
We have sourced the best WNBA odds in America for this game, which are listed here:
| Bet Type | Wings | Sky |
|---|---|---|
| Spread | -2.5 (-115) | +2.5 (-105) |
| Moneyline | -150 | +130 |
| Total | o169.5 (-110) | u169.5 (-110) |
All odds are correct at the time of publication and are subject to change.
Wings vs. Sky picks and best bet
After matching our probabilities against the best available odds, we can reveal our picks for each of the major markets. Plus, find our best bet for the game below:
| Bet Type | Pick | Bet Now |
|---|---|---|
| Spread | Wings -2.5 | -115 |
| Moneyline | Wings | -150 |
| Total | Under 169.5 | -110 |
According to our best WNBA bets, the top play to make on this game is Wings to win.
These picks are based on our probabilities matched against the implied probabilities from the sportsbook odds.
Wings vs. Sky player props
WNBA player props are a popular way to wager on the Dallas vs. Chicago matchup without necessarily betting on the outcome. We have crunched the numbers to project how each team's leading players will perform at Wintrust Arena.
Paige Bueckers is expected to lead the Wings with 20 points, 4 rebounds and 5 assists, while Skylar Diggins-Smith is projected to have 16 points, 3 rebounds and 7 assists for the Sky.
Check out our WNBA player projections for a full range of projected box scores, including points, assists, rebounds and today's WNBA first basket picks.
Wings prediction
Our model's projected player stats for the Wings are:
| Player | PTS | REB | AST | 3PM | DFS |
|---|---|---|---|---|---|
| Paige Bueckers | 20 | 4 | 5 | 1 | 39 |
| A. Ogunbowale | 18 | 3 | 4 | 2 | 33 |
| Jessica Shepard | 12 | 10 | 4 | 0 | 33 |
| Azzi Fudd | 11 | 2 | 2 | 2 | 21 |
| Odyssey Sims | 9 | 2 | 3 | 1 | 20 |
Sky prediction
Projected points, rebounds, assists and three-pointers made for the Sky:
| Player | PTS | REB | AST | 3PM | DFS |
|---|---|---|---|---|---|
| S. Diggins-Smith | 16 | 3 | 7 | 2 | 36 |
| Kamilla Cardoso | 15 | 7 | 3 | 0 | 32 |
| Natasha Cloud | 12 | 4 | 6 | 2 | 31 |
| Gabriela Jaquez | 11 | 4 | 2 | 1 | 23 |
| Jacy Sheldon | 9 | 2 | 3 | 1 | 21 |
Wings vs. Sky game-day updates and essential details
Wednesday's matchup between the Sky and Wings at Wintrust Arena is scheduled to start at 9:00 PM ET.
- Who: Dallas Wings vs. Chicago Sky
- Date: Wednesday, May 20, 2026
- Time: 9:00 PM ET/6:00PM PT
- Venue: Wintrust Arena
Conclusion
We predict the Wings, with a 70% win probability, will likely beat the Sky in Wednesday's WNBA matchup.
Additional tools and information for betting safely can be found in our Responsible Gambling hub.
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Dave Garofolo uses sophisticated AI-driven analytics to make predictions and evaluate player performances in the NBA, MLB, NFL, NHL, NCAAM, and PGA TOUR tournaments, crafting insightful game and prop previews.
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