With the sound of Sydney Taylor’s game-winning buzzer-beaters still ringing in Wintrust, the Sky close out a regular season defined by growth, hardship, perseverance and game-winning performances. The Sky left fans with a bevy of unforgettable moments in a season full of highs and lows.

Here are the top 10 moments that defined the Chicago Sky this year:

No. 10: Aicha Coulibaly Gets Signed to Rest-of-Season Contract

Coulibaly started the year with the Sky on a developmental contract, a roster spot introduced this year that allows teams to carry two additional players beyond the 12-woman roster. Although developmental players are only allowed to be activated for a maximum of 12 games, Coulibaly quickly saw action in 10 games just one and a half months into the season. On June 28, four days after her then-career high of 10 points, three rebounds, an assist, two steals and a block against the Fire, the Sky signed Coulibaly to a rest-of-season contract. In the 2026 season, she averaged 5.2 points and 2.6 rebounds in 13.6 minutes.

No. 9: Sydney Taylor Goes Down as Highest Scoring Undrafted Rookie in WNBA History

Taylor broke many rookie records this year, but this is perhaps her most impressive feat in the league history books. Going from training camp contract to starter, Taylor finished the year as the third-leading rookie scorer in the league with 504 points. As far as undrafted rookies go, Taylor now stands alone as the highest-scoring undrafted rookie to ever play the game.

No. 8: Setting the Single-Game Franchise Scoring High

On June 26, the Sky made franchise history by logging a whopping 124 points in a win against the Toronto Tempo. This game also marked Courtney Vandersloot’s return to action after tearing her ACL last June. The veteran logged seven assists and 10 points in 14 minutes off the bench to complement Taylor’s rookie performance of 29 points and six 3-pointers. Eclipsing a previous record of 115 points, the triple-digit record was a moment of many throughout the night.

No. 7: Setting the Single-Game WNBA Assist Record

In that same iconic game against the Tempo, the Sky also broke the league-wide record for most assists in a single game with 38. Chicago surpassed Seattle’s previous record of 37 when they played the Sky back in 2022.

No. 6: DiJonai Carrington’s Return to the Court

The highly anticipated wait to see DiJonai Carrington in a Sky uniform did not disappoint. After suffering a foot injury during her playoff run with the Lynx last September, Carrington signed with the Sky while in the throes of rehab. In her first game back on July 30, she was a key piece in the 94-88 comeback against her former team, the Connecticut Sun. Carrington logged nine points, three rebounds and one block, with five of her nine points coming in the final moments of the fourth quarter to seal the game.

No. 5: Natasha Cloud’s 35-5-5 Game

Natasha Cloud saw her career high in points on Aug. 18 during a 93-86 win against her former New York Liberty team. With 16 points in the first half alone, Cloud ended the game with 35 points, nine rebounds and six assists to help avenge the multiple one-point losses the Sky faced against the Liberty earlier in the season. In addition to breaking a career record, Cloud also became the first Sky player to ever have a game with 35 points, five-plus rebounds and five-plus assists. Welcome to the Sky’s exclusive 35-5-5 club, Natasha Cloud.

No. 4: Courtney Vandersloot Hits 3,000 Assists

On a usual night heading towards nine assists, Vandersloot made WNBA history against the Connecticut Sun Aug. 25. After dime No. 8 on the night, Vandersloot became the second WNBA player ever to hit 3,000 career assists. Sloot ends the year with 3,007 total, joining only legendary point guard Sue Bird, who sits at 3,234 assists in this accomplishment.

No. 3: Kamilla Cardoso’s ‘Perfect Game’

Heading back to the record-breaking game against Toronto, Cardoso added yet another record to the evening in logging her ‘perfect game’. In an absolute masterclass of efficiency, Cardoso shot 13 for 13 from the field, setting the WNBA record for the most made field goals in a game without a miss. In addition to 30 points, Cardoso put up eight rebounds and one assist on the night.

No. 2: Sydney Taylor’s Game-Winning Three-Pointer to Beat the Las Vegas Aces

With her hands over her face at center court, Taylor takes the No. 2 spot with her buzzer-beating three-pointer against the Aces. With 0.9 seconds remaining, Taylor stepped into a three-pointer off a sideline inbound pass from Natasha Cloud and secured the 84-83 Sky win. Aside from the game-winning shot, Taylor had 29 points and marked five 25-plus-point games this season. Combined, all other undrafted rookies have logged five 25-plus-point games in WNBA history.

No. 1 Sydney Taylor’s (Second) Game-Winning Three-Pointer 20 Days Later to Beat the Valkyries

Taylor’s quick release from three will go down as the most memorable Sky moment this season. Of all her 71 three-pointers, this one was one of the most memorable; further cementing her case for the WNBA All-Rookie team. After her phenomenal game-winning three-pointer that upset the Aces, she showed up to Wintrust just 20 days later to do it again. While the second-place Valkyries fought back from a 21-point deficit, Taylor ended their comeback by draining a side-step three-pointer over Veronica Burton with 1.6 seconds left. In doing so, Taylor became the first rookie in WNBA history to hit two go-ahead game-winning three-pointers.

A season full of individual milestones and broken records gives Chicago a clear foundation of what success and high-level play looks like. With a core that has already proved it can produce under pressure, the focus shifts entirely to turning these historic moments into sustained wins next year.

Chicago Sky vs. Toronto Tempo: 9/22 Game Day Highlights Presented by Demesmin & Dover