1969

By all accounts, during a horrible summer of baseball on the South Side, the White Sox found some relief — north of the Illinois-Wisconsin border. With an 8-3 win over the Seattle Pilots as one of 11 games played that season at Milwaukee County Stadium, the White Sox stretched their “Milwaukee White Sox” winning streak to five games (not consecutive wins, however, as each game at Milwaukee was a single contest, with the White Sox opposing every other AL team up north once during the season).

Chicago struck early and often, going up, 8-1, through three. Future Dodgers relief ace Mike Marshall took the brunt of the damage as Seattle’s starter, while the White Sox took advantage of three Pilots errors in the early going, and four total in the game.

The five wins equaled what would become the team’s longest outright winning streak (later that year, in September) and was not an indication of how good the team was; while this win improved the White Sox to 24-32, they still sat two games behind the expansion Pilots. In the end, the White Sox finished 1969 with a 68-94 record that was good for sixth place in the AL West and just four games better than Seattle.

1989

At 37, former Tigers farmhand Rick Wolff (drafted out of Harvard in 1972) makes a one-series comeback with the South Bend White Sox of the Midwest League (Single-A) for the purposes of a Sports Illustrated article. Wolff pinch-hit at the end of his first game, then starts the next two, batting ninth and then creeping up to eighth — and finishes the series 4-for-7 with a ground-rule double, three RBIs and a .571/.556/.714 slash line. His one error at second base comes when a pickoff throw travels through the pocket of his 20-year-old glove. Wolff himself was 15.1 years older than league average.

This was no end-of-season stunt in a lost season, a la Minnie Miñoso two decades earlier. South Bend won its division in 1989 with an 85-47 record, and featured such future White Sox as Scott Radinsky and Roberto Hernández, along with four other future major leaguers.

1997

After numerous charity and exhibition games, the White Sox and Cubs played for real for the first time in the regular season. The Cubs crushed their former starter Jaime Navarro, jumping to a 6-0 lead and hanging seven earned on him in an 8-3 win. Lyle Mouton had a solo blast with the game out of hand in the sixth for the first Sox-Cubs interleague homer for the White Sox, while the Cubs went roundtripper-free in their first Crosstown interleague game. This was also the first interleague game ever played at Sox Park, and thus Mouton’s was the first home four-bagger in interleague play for the White Sox.

Since then, the two teams have played each other every season multiple times. Overall, the Cubs have just this season taken back the all-time IL series lead from the White Sox.

2023

The White Sox struck out 16 times in a 3-2 loss in Seattle against the Mariners. This came on the heels of striking out 16 times the night before in a 5-4 loss to the Dodgers in Los Angeles. That tied the club mark first set in 2018.

Another oddity was the Sox hit six home runs in the two games but because they couldn’t get runners on base, every single home run was a solo shot!

Luis Robert Jr. and Jake Burger both homered once over the two games — and struck out seven times apiece!