The season was initially scheduled to feature an all-time high 36 regular-season games, tipping off at the Sky's home Wintrust Arena on May 15, 2020.
[2][3] Under a plan approved on June 15, the league has been holding a shortened 22-game regular season at IMG Academy, without fans present, since July 24.
In the offseason, the team added Azurá Stevens and Sydney Colson while losing Katie Lou Samuelson.
[9][10][11] Free agents Allie Quigley, Courtney Vandersloot, and Stefanie Dolson were all re-signed to multi-year deals.
[20] The WNBA-focused publication Winsidr gave the Sky a B+, rating the retentions of key players and addition of Sydney Colson highly, but criticizing the value of the trade for Stevens.
The Sky received a grade of B in three post-draft evaluations from ESPN, CBS Sports, and SB Nation.
[31] The Sky then won four consecutive games, including blowout wins against the Atlanta Dream and the New York Liberty, to improve to 10–4.
On August 28, the Sky traded two draft picks and Jantel Lavender, who had been out for the season due to injury, in exchange for Stephanie Mavunga.
[33] On August 29, two key players for the Sky, Diamond DeShields and Azurá Stevens, exited the IMG Academy bubble.