Dallas Wings vs Chicago Sky Prediction 5/20/2026 Today’s WNBA Picks

The Dallas Wings and the Chicago Sky meet Wednesday in WNBA action from the Wintrust Arena. We will look at this from a betting perspective and determine the best bets for this game. Here’s a Dallas Wings vs. Chicago Sky prediction.

Matchup History

The Chicago Sky won the most recent meeting between these two teams by a final score of 87-76 back on July 9th, 2025, for their 6th straight win in this head-to-head matchup.

Dallas Wings Recap

The Dallas Wings come into this game looking to add on to a 92-69 win over Washington last time out to sit at 2-2 this season. After this game, the Wings will head on the road for a game against the Atlanta Dream.

Wings Snap Two-Game Skid

Arike Ogunbowale has 16 PPG along with 2.5 APG while Paige Bueckers has 20 PPG along with 2.8 RPG and 5.5 APG. Jessica Shepard’s added 11 PPG with 9.8 RPG and 5.5 APG to lead the Wings in rebounding and assists and to round out the group of double-digit scorers for the Wings so far this season. Odyssey Sims had added 9.5 PPG with 3.3 APG and Maddy Siegrist has 9 PPG with 2.5 RPG while Azzi Fudd’s chipped in 7.7 PPG as well this season.

Chicago Sky Recap

The Chicago Sky come into this game looking to add on to their 86-79 win over the Minnesota Lynx last time out to sit at 3-1 this season. After this game, the Sky will have a rematch against the Lynx, this time at home.

Sky Looking For Big Home Debut

Skylar Diggins has 12 PPG with 6 RPG and a team-high 5.7 APG to lead the Sky in assists. Kamilla Cardoso has 12 PPG with 10.3 RPG to lead the Sky in rebounding and Jacy Sheldon has 10.8 PPG with 3 RPG and 3.3 APG. Gabriela Jaquez also has 12.5 PPG with 5.8 RPG to cap off the group of double-digit scorers for Chicago so far this season.

Dallas Wings @ Chicago Sky Betting Trends: May 20, 2026

Why the Chicago Sky will win

• The Sky have won eight of their last nine games as underdogs against the Wings.
• The Wings have lost each of their last 12 Wednesday night games against teams that held a winning record.
• The Wings have failed to cover the spread in each of their last seven games as road favorites following a home win.
• The Sky have covered the spread in each of their last six games against the Wings.

Why the Dallas Wings will win

• The Sky have lost each of their last 12 games after winning as underdogs.
• The road team has won four of the Sky’s last five games.
• The Sky have failed to cover the spread in each of their last seven home games after winning as underdogs.
• The favorites have covered the spread in four of the Wings’ last five games at Wintrust Arena.

Total Points Facts

• Each of the Wings’ last six road games following a home win have gone OVER the total points line.
• Each of the Sky’s last eight Wednesday games have gone UNDER the total points line.

Chicago Sky Player Facts

• Jacy Sheldon ranks T1st amongst qualified players for FT% (100.0%) this season.
• Skylar Diggins has recorded 2+ assists in 91 consecutive appearances – longest active streak of any player in the league.

Dallas Wings Player Facts

• Paige Bueckers has hit 3+ three-pointers in two consecutive appearances – equal-longest active streak of any player in the league.
• Jessica Shepard has recorded two games with 4+ assists and zero turnovers this season – most of any player in the league.

Matchup/League Facts

• The Chicago Sky rank 1st for opponent assists per game this season (15.5).
• The Chicago Sky rank T14th for steals per game this season (5.8).
• The Dallas Wings rank 14th for blocks per game this season (2.5).
• The Dallas Wings rank 1st for assist to turnover ratio this season (1.9).

Dallas Wings vs. Chicago Sky Prediction

I’m on the Sky at home here. I think this line is an overreaction to the Rickea Jackson injury. Yes it’s a big blow for Chicago, as Jackson is done for the year, but this is still a very talented Sky team that has size inside with Cardoso and the Wings are still one of the least effective rebounding teams in the WNBA this season. All in all, I think the Sky get it done at home here so give me the points.

Chris Ruffolo's Pick: Chicago +2.5