| Date | Location | Score | Winner |
|---|---|---|---|
| June Series — Wrigley Field | |||
| June 16 | Wrigley Field | PPD — Rain. Makeup: Sept 3 at Wrigley. First ever postponed Crosstown Classic game. | |
| June 17 | Wrigley Field | Sox 4–1 | White Sox W: Danks L: Dempster SV: Jenks (15). Danks: 7 IP, 1 ER, 5 H, 9 K, 0 BB. Dempster: 6 BB. Walk 6, lose. That’s how it works. |
| June 18 | Wrigley Field | Cubs 6–5 | Cubs Floyd goes 7 IP, 1 ER but the Cubs rally in the 8th. Derrek Lee HR off the basket. Geovany Soto solo shot to tie it. Soriano single plates Reed Johnson for the walk-off. Series tied 34-34 all-time. |
| June Series — U.S. Cellular Field | |||
| June 26 | U.S. Cellular Field | Cubs 5–4 | Cubs |
| June 27 | U.S. Cellular Field | Sox 8–7 | White Sox |
| June 28 | U.S. Cellular Field | Sox 6–0 | White Sox Sox shut out the Cubs to take the Cell series 2-1. |
| September Makeup — Wrigley Field | |||
| Sept 3 | Wrigley Field | Sox 5–0 | White Sox Rookie Carlos Torres: 7 shutout IP in his 3rd major league start. Soriano slips on a fly ball in the 8th — Pierzynski safe at 3rd on the error, Konerko RBI single follows. Dempster takes his frustration out on the water fountain. Sox take the all-time lead 37-35. |
The 2009 Crosstown Classic had a little bit of everything — a rain postponement, a comeback win, a rookie shutout, and a water fountain that took a beating. Seven total games. Sox win 4-2.
June 16 at Wrigley: rained out. The first ever postponed Crosstown Classic in the history of the interleague series. The makeup was September 3, also at Wrigley, and the Sox won 5-0 behind rookie Carlos Torres throwing 7 shutout innings in just his 3rd major league start.
June 17: John Danks threw 7 innings with 9 strikeouts and zero walks. Ryan Dempster threw with 6 walks. Walk 6 batters, you lose. Don’t walk any, you win. Alexi Ramirez hit his 6th HR. Jenks closed it. Sox win 4-1.
June 18 was the good one. Floyd pitched brilliantly, Sox led 5-1 heading into the 8th. Then the Cubs woke up. Hoffpauir reached on an error. Derrek Lee homered to the basket in right. Geovany Soto hit a solo shot to tie it. Reed Johnson singled as a pinch hitter, Soriano drove him in. Cubs win 6-5. All-time series tied at 34-34.
Then the Sox swept the Cell series in June and sealed it with the September makeup. In the finale, Soriano slipped going after a Pierzynski fly ball in the 8th, the Sox scored, Konerko added an RBI single. Aramis Ramirez summed it up: “The last time I checked, we didn’t score any runs, so even if [Soriano] makes that play, we lose.” Ryan Dempster took his frustration out on the water fountain. The water fountain won.