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May 24, 2022; Chicago, Illinois, USA; Members of the Chicago Sky pose for a picture as the 2021 WNBA Championship Banner is revealed during a championship ring ceremony before a WNBA basketball game against the Indiana Fever at Wintrust Arena. Mandatory Credit: Kamil Krzaczynski-Imagn Images
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With these awards, the following players in the Chicago Sky's history have been decked with the hardware for their accolades. Here's a look at which Sky players have the most awards, records, and honors.

Scott Conrad
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Sep 11, 2025; Chicago, Illinois, USA; Chicago Sky forward Maddy Westbeld (21) looks to pass the ball against the New York Liberty during the second half at Wintrust Arena. Mandatory Credit: Kamil Krzaczynski-Imagn Images
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Maddy Westbeld still has some ways to go, but she proved to be a decent backup during her first season with the Chicago Sky.

Alex Sabri
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Sep 11, 2025; Chicago, Illinois, USA; Chicago Sky head coach Tyler Marsh walks on the sidelines during the second half at Wintrust Arena. Mandatory Credit: Kamil Krzaczynski-Imagn Images
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After winning the 2021 WNBA title, the Chicago Sky have missed the playoffs two seasons in a row. According to early predictions, a third straight year missing the postseason is upon them.

Scott Conrad
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