Wings vs. Sky Prediction, Odds and Best WNBA Prop Bets for Thursday, May 29

The Wings are road favorites on Thursday against the Sky.

The Wings are road favorites on Thursday against the Sky. / David Butler II-Imagn Images

Fresh off their first win of the 2025 season, the Dallas Wings hit the road to play Angel Reese and the Chicago Sky on Thursday night.

Chicago is coming off a loss to the Phoenix Mercury on Tuesday, which dropped it to 0-4 in the 2025 campaign. It was the fourth time in as many games that the Sky gave up over 90 points.

Meanwhile, the Wings rode a huge game from rookie guard Paige Bueckers (21 points, five rebounds, seven assists) to a win over the winless Connecticut Sun. Even though the Wings are just 1-4, they have one of the better offenses in the WNBA so far this season (fifth in offensive rating).

Oddsmakers have favored the Wings on the road in this matchup, but should bettors trust them to win two games in a row?

Here’s a look at the odds, players to watch in the prop market, and my prediction for Thursday’s contest. 

Wings vs. Sky Odds, Run Line and Total

Odds via DraftKings Sportsbook.

Run Line

• Wings -3 (-110)
• Sky +3 (-110)

Moneyline

• Wings: -162
• Sky: +136

Total

• 169.5 (Over -110/Under -110)

Wings vs. Sky How to Watch

• Date: Thursday, May 29
• Time: 8:00 p.m. EST
• Venue: Wintrust Arena
• How to Watch (TV): Prime Video
• Wings record: 1-4
• Sky record: 0-4

Wings vs. Sky Injury Reports

Wings Injury Report

• Ty Harris – day-to-day

Sky Injury Report

• Hailey Van Lith – day-to-day

Wings vs. Sky Best WNBA Prop Bets

These prop bets are suggestions based on past player performance. This story was written before prop odds were released for this game. 

Wings Best WNBA Prop Bet

• Paige Bueckers OVER Assists

This season, Bueckers is averaging 6.4 assists per game, picking up at least five dimes in each of her last four games.

Now, she has a great matchup against a Sky defense that is dead last in the WNBA in defensive rating and 12th in opponent assists per game, allowing over 23 per night.

Bueckers has played heavy minutes for the Wings, and she may already be the team’s best distributor of the rock. She has three games with seven or more dimes, and I expect her to pick apart this weak Chicago defense on Thursday.

Wings vs. Sky Prediction and Pick

Earlier today, I shared in my WNBA Best Bets column – Peter’s Points – why the Wings are the bet to make in this matchup on Thursday night: 

For the second straight game, Dallas is favored on the road, and I’m buying the Wings to pick up a win on Thursday.

Dallas has not gotten off to a great start, losing its first four games, but it dominated a struggling Connecticut team by 22 points on Tuesday. Even though the Wings are just 1-4, they have single-digit losses to playoff-caliber teams in Minnesota, Seattle and Atlanta.

Chicago is not that.

The Sky have been brutal on both ends of the floor this season, ranking dead last in the WNBA in defensive rating (113.6) and second-to-last in offensive rating (89.5). The Sky have certainly looked like a lesser team on the offensive end without last season’s leading scorer – Chennedy Carter – in the fold. 

Dallas is just 11th in defensive rating in 2025, but it has the No. 5 offense in the league, led by Bueckers and Arike Ogunbowale. I expect the Wings to dominate on that end against a weak Chicago defense that has given up over 90 points in every game in 2025. 

Pick: Wings -3 (-110 at DraftKings)

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Odds refresh periodically and are subject to change.

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Find Peter Dewey's WNBA betting record here (futures included). You can also follow my daily plays on  BetStamp here.

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