Wings vs. Sky prediction: Paige Bueckers projected to score 20 points in Wednesday's WNBA game [5/20/2026]

The Chicago Sky and Dallas Wings will lock horns in the WNBA at Wintrust Arena on Wednesday, with tipoff at 9:00 PM ET.

Based on updated simulation results, Dimers' proven WNBA model predicts the Wings as the most likely winner of the Wings vs. Sky game.

The Sky, who have star players such as Skylar Diggins-Smith, Kamilla Cardoso and Natasha Cloud, will face off against the Wings, who feature Paige Bueckers, Arike Ogunbowale and Jessica Shepard.

Bueckers, the Wings' No. 1 pick in the 2025 WNBA draft, is expected to deliver a standout performance 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 trusted machine learning and data, 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 gives the Wings a 70% chance of beating the Sky.

According to our model, the Wings (-2.5) have a 61% chance of covering the spread, while the 169.5-point over/under 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 (-112)	+2.5 (-105)
Moneyline	-148	+125
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 predictions against the best current 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	-112
Moneyline	Wings	-148
Total	Under 169.5	-110

According to our WNBA best 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

Looking for Wings vs. Sky WNBA prop bets? 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 action 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.