A look back at the Sky in the postseason

The team’s playoff history has many chapters, but no title.

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Allie Quigley

Allie Quigley #14 of the Chicago Sky looks to pass the ball around Jasmine Thomas #5 of the Connecticut Sun in the first half during Game One of their First Round playoff at Feld Entertainment Center on September 15, 2020 in Palmetto, Florida.

Julio Aguilar/Getty Images

It’s sometimes easy to forget the Sky haven’t been an established WNBA franchise that long. 

Their inaugural season was in 2006. In 2008 the team drafted Sylvia Fowles as the face of the franchise, but by 2015 she was traded to the Minnesota Lynx. 

In 2011 Courtney Vandersloot was selected third overall. Elena Delle Donne followed in 2013, helping them reach the playoffs that year for the first time in franchise history. 

In their 16th WNBA season the Sky are back in the playoffs for the seventh time, looking for their first-ever WNBA title. 

Here’s a look back at the Sky’s playoff runs. 


After adding Delle Donne with the second overall pick to an already experienced roster with Fowles, Vandersloot and Swin Cash, the expectation was that the Sky would make the playoffs. 

They did more than expected, clinching the Eastern Conference regular-season title and earning the No. 1 overall seed heading into the postseason. Their 24-10 record is still the best in franchise history. In a best-of-three conference semifinal series against the reigning champion Indiana Fever, the Sky were swept. 

Indiana went on to lose to Atlanta 2-0 in a best-of-three series. Minnesota won its third WNBA championship beating the Dream in a best-of-five series 3-0. 


The Sky started the season 5-1 but lost 13 of their next 16 games after injuries kept Fowles, Delle Donne and Vandersloot sidelined for significant time. 

Fowles missed the team’s first 13 games recovering from an offseason surgery, Vandersloot missed 15 with a sprained MCL and Delle Donne — who was battling Lyme disease — played in three games between the end of May and the All-Star Game. The team carried an 8-14 record into the second half of the season and finished the regular season 15-19 tied for fourth in the Eastern Conference. 

The Sky beat the Dream and then the Fever 2-1 in best-of-three series in the Eastern Conference semifinals and finals before being swept by Phoenix 3-0 in the Finals. 


The Sky welcomed hometown player and WNBA champion Cappie Pondexter to the roster. After Fowles sat out the first half of the season, she was traded to the Lynx in a three-team deal. 

The Sky’s 21-13 regular-season record was the second-best in franchise history. They earned the No. 2 seed in the Eastern Conference and lost 2-1 to the Fever in the conference semifinals. 

The Fever then lost 3-2 to Fowles and the Lynx in the Finals. 


In Pokey Chatman’s final year at the helm, the team finished the regular season 18-16. 

The team had three Olympians compete at the Summer Olympics in Rio. Delle Donne helped Team USA win a gold medal, while Erika De Souza and Clarissa Dos Santos both represented Brazil. When the team returned from the Olympic break it started the second half of the season 4-0 and finished 13-7 to earn a fourth consecutive trip to the playoffs. 

Under the league’s new playoff format the Sky earned a first-round bye before beating the Dream 108-98 in a second-round, single-elimination game. They then lost in a best-of-five semifinal series 3-1 to Candace Parker and the Los Angeles Sparks. Parker led the Sparks to their third WNBA title, beating the Lynx 3-2 in the Finals series. 


James Wade was hired ahead of the 2019 season making him the third head coach in three seasons. He led the team to a 20-14 record and earned coach of the year honors. 

The Sky were led by Vandersloot and Allie Quigley, but had an abundance of young talent in Diamond DeShields, Gabby Williams and Kahleah Copper. In her second season, DeShields led the Sky in scoring at 16.2 points per game. The Sky coasted by the Mercury in the first-round single-elimination game 105-76. 

It was the second time in franchise history the Sky scored 100 points in a playoff game. The first was in their 2016 second-round matchup against the Dream. 

In the second round the famous Dearica Hamby heave put the Aces up 93-92 with five seconds left. The Aces held on to the lead and sent the Sky home in one of the organization’s most memorable losses. Players are still challenged by the memory of this one-point loss. 


After players agreed to a shortened 2020 season that would be played in the WNBA bubble in Bradenton, Florida, the Sky got to work to rebound from their early 2019 playoff exit. The season was marked by uncertainty and instability. But more than anything else, it was a year of advocacy. The league and players association announced the creation of the WNBPA Social Justice Council with the purpose of pushing for change on issues of race, voting rights, LGBTQ advocacy and gun control.

After multiple players left the bubble, the Sky finished the season a disappointing 12-10 and lost in the first round of the playoffs to the Connecticut Sun. 


After signing Parker to a two-year contract, the Sky became instant contenders. But injuries and inconsistency has them at the No. 6 seed heading into the playoffs. 

It’s all but locked in that they will face the Dallas Wings in a first-round single-elimination matchup. As the No. 6 seed they will have home-court advantage. The Sky have a 5-9 record at home and lost to the Wings twice earlier in the season. 

One thing the team has stressed — and Vandersloot has seen them do it before — is getting hot at the right time. Winning their final game of the season against the Fever is a good place to start.

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