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The 20 Greatest Chicago Sky Highlights of All Time

ByEdwin Garcia|@SkyInTheChi| November 29, 2020
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Chicago Sky highlights display some of the best basketball on the planet. With more than ten years of history under their belt, the team is now a WNBA institution and regularly puts on dazzling performances.

While it may feel like the Chicago Sky have been a part of the WNBA since day one, that’s surprisingly not the case. The WNBA began playing games in 1997, which is eight years before the Chicago Sky team was even founded — in 2005.

Since then, the Chicago Sky have captivated audiences in the Chicagoland area and beyond. Providing many memorable moments of skilled athleticism.

So today, we’ll share the 20 greatest Chicago Sky highlights of all time. You’ll discover old jerseys, a three point shooting contest winner you need to know, and even enjoy an appearance of the iconic Navy Pier. So let’s take a trip down memory lane and celebrate the best moments in Skytown History!

Discover the best Chicago Sky highlights

Explore the best Chicago Sky moments, starting way back from the beginning. We’ll go from the first Sylvia Fowles dunk, through to the Chicago Sky’s first appearance in the finals, to their new logo, and beyond.

1. Chicago Sky history begins with the inaugural season 

The Chicago Sky began playing in the WNBA during the 2006 season. The season was filled with lots of excitement, but very few wins on the court. Still, it’s not every day a city gets a major sports franchise. So the Chicago Sky joining the WNBA was a huge win for the young league and for the city of Chicago. 

The Chicago Sky played in the heart of Chicago at the UIC Pavillion. And was coached by Dave Cowens who was also the teams general manager. Take a look back at where it all began in the video below. 

2. Sylvia Fowles dunks in the All-Star Game 

The slam dunk is one of the most exciting plays in all of sports. And during the 2008 WNBA All-Star game Sylvia Fowles of the Chicago Sky did just that. She dunked the ball late in the game and the crowd went crazy.

Sylvia became the third player in WNBA to dunk in an all star game. She also was the very first Chicago Sky player to make the all star game. Making her a very important part of Chicago Sky history. Watch her historic dunk below. 

3. Chicago Sky call All State Arena home 

In 2010 the Chicago Sky moved to All State Arena. This move was a surprise to many. Some viewed the move out of the city as a negative. While others thought it was improvement due to the All State Arena being a superior venue compared to the UIC Pavillion.

Either way this marked the start of a new era. Listen to Chicago Sky majority owner Michael Alter explain the rationale of the move in the video below. 

4. The “Point God” arrives in Skytown 

Courtney Vandersloot is one of the most important players in Chicago Sky history. She’s a two time all-Star, assist leader, and the point god of the WNBA. Her arrival in 2011 marked significant changes in the team.

During her rookie year the Chicago Sky hired their fourth coach in team history, Pokey Chatman, and Sylvia Fowles continued to be a star. Courtney quickly became a starter, and has been a starting point guard for the team ever since. Highlights of her rookie campaign are hard to come by. But here is a buzzer beater she hit against the Indiana Fever. 

5. Elena Delle Donne enters Chicago Sky history 

It’s hard to imagine now, but Elena Delle Donne’s time with the Chicago Sky started off bright. She was a rookie phenom averaging 18 points a game and became she led all players in votes for the All-Star game. She was the first rookie to do that in WNBA history. 

Thanks to her great play the Chicago Sky qualified for the playoffs and earned the top seed in the Eastern Conference making it the most successful Chicago Sky season to date. View Elena Delle Donne’s highlights from her historic rookie season below. 

6. Chicago Sky get their first taste of the Playoffs 

Winning is everything. It leads to loyalty and love for a team. It helps reinforce pride and strength with the community. And it leads to attracting star players to your franchise. We remember the winning years, and if you go all the way, banners hang in rafters and legends are born.

That didn’t happen for the Chicago Sky in 2013. But their first playoff appearance helped establish a winning culture. And gave the Chicago Sky a taste of the level of intensity the playoff provides. Watch a recap of game two of the Phoenix versus Chicago Series below. 

7. The Chicago Sky’s 2014 WNBA Finals appearance 

2014 brought the Chicago Sky their most successful season in franchise history. Elena Delle Donne had issues with her Lyme disease condition and missed significant portions of the season. But she was able to miraculously return and lead the Chicago Sky to the WNBA finals.

Unfortunately Elena suffered some back issues in the previous round and was unable to be 100 percent for the WNBA finals series. The Sky lost in a sweep, but reached heights they’d never achieved before. 

8. The Chicago Sky turns ten

For a team to exist for a decade is difficult. So much can go wrong and so much is out of anyone’s control. It seemed like there were always constant rumors that the WNBA wouldn’t survive. And lots of skepticism if Chicago would support a women’s basketball team.

Luckily, the rumors were just that and Chicago did come out — and still comes out to support the Chicago Sky. The team lasting for ten years proves that. Here is a wonderful video the Chicago Sky made to celebrate this anniversary. 

9. The Chicago Sky hang their first banner 

With the ten year anniversary well underway the Sky decided to celebrate by adding their first banner to the AllState Arena rafters. They decided to put the 2014 Eastern Conference Championship up for everyone to see.

To celebrate the occasion the Chicago Sky made a video on their YouTube channel breaking down how they ultimately won the East. Watch it below. 

10. Elena Delle Donne asks for a trade 

Perhaps not a highlight in the traditional sense, but definitely a definitive moment in the franchise’s history,  was when Elena Delle Donne requested a trade in 2017. Dissatisfied with the roster, the commitment to winning by the organization, and the “revolving door” of coaches and general managers, Elena wanted out of Chicago. On February 2nd, she got her wish and was traded to the Washington Mystics. The Chicago Sky received Stefanie Dolson, Kahleah Copper, and the No. 2 pick in the 2017 draft.

 While this trade was beneficial to both parties involved, it was a harsh reminder of how quickly things can turn and how a dedication to winning and love and care for your players is required at all times. As a result of this trade, the Chicago Sky fan base became more aware of these realities along with ownership. Part of learning how to win is dealing with losses. And Elena Delle Donne leaving was a huge loss for the team.

It also started a new era for the team. A fresh start and an opportunity to refresh, regroup, and rebrand. 

11. The Chicago Sky come back to Chicago 

The Chicago Sky started in Chicago, left for the suburbs, and ultimately came back home. They didn’t return to the UIC Pavillion — instead moving to the newly made Wintrust Arena.

The arena seemed like a perfect fit from the start. It’s bigger than UIC Pavillion, but not enormous like AllState Arena, and is located in a great spot. Watch a clip of the Chicago Sky’s first Media Day at Wintrust Arena below. 

12. The Chicago Sky get a new logo 

As part of their rebrand, the Chicago Sky got a new logo. The logo was met with mixed reactions initially, but most fans warmed up to the new logo eventually.

Change can be uncomfortable. But by now it’s clear that most would agree the new logo is an improvement from the previous one. Check out the logo unveiling video below. 

13. James Wade becomes Head Coach and GM 

In November 2018, James Wade became the head coach and general manager of the Chicago Sky. He quickly turned the team around taking the Sky from 13-21 to 20-14. The Chicago Sky made it to the second round that year and he was named Coach of the Year.

Hiring James Wade is one of the best moves the Chicago Sky have made in their history. So watch his introduction video below. 

14. SkyTown dominates the All-Star Game 

2018 is arguably the best year in Chicago Sky History. Nothing demonstrates this better than the 2018 All-Star game.

The Chicago Sky had a record three players make the team. And they shined all weekend long. It was a celebration of how far the players and the team had come in such a short time. Below you can watch Allie Quigley’s post All-Star Game Interview. 

15. Allie Quigley wins the three point contest 

Allie is arguably the best shooter in the game. She has made it clear that if she’s not your favorite, she’s definitely in the running. During the 2018 three point contest she won her second three point contest in a row. And did so by just absolutely dominating the final couple of racks in the tiebreaker round.

You can watch every three she took in the three point contest below. Enjoy. 

16. Chicago Sky vs Aces 2018 rivalry heats up

The regular season and playoff matchups between the Chicago Sky and the Las Vegas aces were intense. Both teams were very good, evenly matched, and had a bark that only rivaled their bite.

During the regular season, Stefanie Dolson and Cheyenne Parker both got into physical and verbal altercations with Las Vegas big Liz Cambage. The trash talk and bumps got pretty heated. So when the two teams faced each other in the playoffs it was a matchup many were looking forward to. It didn’t disappoint. 

All the games were close. Including the final elimination game, which was decided by one point. The game went back and forth with twenty lead changes. Ultimately it ended with the now infamous “Hamby Heave” where Aces player Dearica Hamby stole the ball from Courtney, drove down the court, and heaved a shot from the sideline — making the game winner with just seconds left.

It didn’t work out the way the Chicago Sky wanted, but it was an instant classic and demonstrated how great both teams really were. You can watch the game three highlights below. 

17. James Wade is Coach of the Year 

James Wade accomplished so much his first season as head coach of the Chicago Sky. He turned around a franchise in one of the biggest WNBA markets. Because of this spectacular season, James Wade won Coach of the Year in his first year as head coach of the Chicago Sky. His acceptance speech was emotional and powerful. It really is a must watch speech. 

18. Courtney Vandersloot gets single season assists record

When it’s all said and done, Courtney is going to have a lot of assist records. In 2018, she added her name to the history books by getting the most assists in a season with 258. Then she broke that record the following year, chalking up 300 in 2019!

There’s a good chance that record will stand for a while. But if the 2021 season is a full season she just might beat it then again. Here are some highlights from her 2019 campaign. 

19. Chicago Sky life In The Wubble 

The 2020 season was unlike any other. The entire world was ripped by a global pandemic. Because of the coronavirus COVID-19, the WNBA and NBA decided to play out their seasons in a bubble.

This meant the players had to be apart from all people, except their teammates, coaching staff, and personnel allowed in the bubble. It was a challenge that was unprecedented in sports. The fact that they were able to pull off playing in the bubble safely is a testament to what can happen when people come together, make sacrifices, and listen to health officials and scientists.

People began referring to the WNBA bubble as the Wubble. As a cute name for the situation using the letter  W to represent bubble the Women were in. There are so many great videos out there about “Life in the Wubble” it’s hard to pick just one. But here’s one of our favorites. 

20. Courtney Vandersloot sets single game assist record (again!)

Courtney has been the point god for years. She’s been an assist leader for the team and for the league. On August 31st, 2020 she did something she never did before. She broke the WNBA record for assists in a game with a whopping 18! It was an incredible performance and really needs to be watched and rewatched. You can do just that below. 

Now you know the 20 greatest Chicago Sky highlights

So there you have it! The greatest Chicago Sky highlights of all time. By now you’ve taken a trip down memory lane, learned more about the team, and celebrated the Chicago Sky’s best moments. 

Want more WNBA history? Check out our article on WNBA dunks.

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