Skylar Diggins reached a new milestone during the Chicago Sky’s 85-80 victory over the Connecticut Sun on Friday night. The Sky had gone through five straight games without a victory, and this time around, they really have Diggins to thank for helping them finally get back into the win column.

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Diggins delivered a whopping 24 points, three rebounds, and four assists, one of her best performances of the season. According to the WNBA’s official X page, Diggins, with her fifth free throw of the game, moved past Cappie Pondexter to become 10th on the WNBA’s all-time free throws made list. In total, she now has 1,461 career free throws made.

Skylar cracks the Top 10 📈With her fifth free throw of the game, Skylar Diggins has passed Cappie Pondexter for 10th on the WNBA’s all-time free throws made list.2026 WNBA Commissioner’s Cup presented by @coinbase pic.twitter.com/i30u26DWxW— WNBA (@WNBA) June 6, 2026

Skylar Diggins was especially efficient at the free-throw line against the Sun in that game. She finished the milestone night shooting 10-of-11 from the charity stripe and also made both of her three-point attempts. Her efficiency from those spots played a major role in Chicago’s victory, even though she shot 37.5% from the field overall.

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Speaking on her performance during the postgame press conference, Diggins laid it out plainly. “My game was for me to play better for this team,” she said. We’ve been trying to figure it out. Obviously, there’s a lot of adversity that we are facing that is beyond our control. So just trying to be aggressive and impose my will.”

The Sky has gone through a rough stretch of injury troubles. What was a rather decent start to the season had turned into a five-game losing streak. They lost Rickea Jackson to a season-ending ACL injury, and Gabriela Jaquez, DiJonai Carrington, and Courtney Vandersloot are also currently sidelined.

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But even as Skylar Diggins expressed a desire to play better in this game, Diggins has already put together quite a decent number of performances for Chicago this season. In fact, she is currently averaging 14.1 points, 4.1 rebounds, and 5.0 assists per game.

Overall, with that victory, the Sky now holds a 4-6 record on the season. They will play their next game against the Toronto Tempo, and they will be hoping to carry the momentum from this win into that matchup as they look to secure another victory.

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Tyler Marsh Applauds Skylar Diggins’ Impact in Crucial Comeback Win Over Connecticut Sun

The Chicago Sky actually started that Connecticut Sun game on the back foot. They ended the first quarter trailing 25-11 and looked to be in serious trouble early on. But despite that difficult start, they managed to turn things around and come away with the victory. And of course, Skylar Diggins had a huge role to play in making that happen.

Speaking at the postgame press conference, head coach Tyler Marsh acknowledged Diggins’ contribution to the game: “She definitely set the tone for us to really hang in there. We could have easily folded after the first quarter. I thought her aggressiveness offensively, and Jacy set the tone for us defensively.”

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Marsh also gave some credit to the rest of the team for “great contribution across the board.” Notably, veteran guard Natasha Cloud finished the game with 13 points, five assists, and two steals. Azurá Stevens contributed 13 points and 10 rebounds, while Kamilla Cardoso ended the game with 10 points and three assists.

After finally putting an end to their five-game losing streak, the Sky will be looking to build on this result and put together a winning run. Hopefully, the team can keep this momentum going in their next game agaist the Tempo. Another strong performance could go a long way toward getting their season back on track.

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Olutayo Inioluwa Emmanuel

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Olutayo Inioluwa Emmanuel is a WNBA journalist at EssentiallySports, bringing a fan-first perspective to coverage of the Women's National Basketball Association. With prior experience reporting on high school sports, college basketball, and the National Basketball Association, he has developed a reputation for timely reporting and audience-focused storytelling. His coverage spans match updates, breaking developments, player analysis, and roster moves, while also tracking the evolving dynamics shaping teams and athletes across the league. Beyond the immediate headline, Olutayo places developments within a broader context by examining roster decisions, team trends, and structural shifts that influence performance across women’s basketball. He also pays close attention to the under-the-radar storylines that matter most to dedicated fans of the sport. Before joining EssentiallySports, Olutayo covered the National Football League and college football, an experience that strengthened his instincts for breaking news and fast-paced reporting while maintaining clarity and accuracy under tight deadlines. His background as a content writer and editor across multiple digital platforms has further shaped his command of structure, tone, and research-driven reporting. Currently pursuing an MBA at Obafemi Awolowo University, he approaches the WNBA with an analytical perspective that connects on-court performances to the broader systems and management decisions shaping the league.

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