Brewers Face Daunting Task That's Only Happened One Other Time in MLB History

That's just the luck of the draw

Jun 6, 2025; Milwaukee, Wisconsin, USA; General view of American Family Field during the fourth inning of the game between the San Diego Padres and Milwaukee Brewers. Mandatory Credit: Jeff Hanisch-Imagn Images | Jeff Hanisch-Imagn Images

Over the next two days, the Milwaukee Brewers are scheduled to face two of the toughest starting pitchers in the entire league. And when that happens, they'll become a part of major league history.

The Brewers are set to go up against Detroit Tigers ace Tarik Skubal on Thursday and Pittsburgh Pirates star Paul Skenes on Friday. As long as both pitchers make their scheduled starts, Milwaukee will be the second team in MLB history to face the reigning Cy Young Award winners in back-to-back games, as pointed out by Brewers reporter Sophia Minnaert.

The other time that defending Cy Young Award winners pitched against the same team in consecutive games was just last year, though. The Boston Red Sox faced Skubal and then Atlanta Braves southpaw Chris Sale last May. And if that two-game stretch is any indication, Brewers fans might not be too thrilled about these upcoming matchups.

Brewers will look to flip the script this time around

Apr 18, 2026; Boston, Massachusetts, USA; Detroit Tigers starting pitcher Tarik Skubal (29) pitches during the first inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

It might not be the biggest surprise to find out that when the Red Sox became the first team in MLB history to face two reigning Cy Young Award winners in back-to-back games last year, they lost both of those matchups. On May 14, 2025, Boston lost 6-5 to the Tigers. Skubal gave up five runs on seven hits in 6 1/3 innings, but also struck out 11 Red Sox. Then, on May 16, 2025, the Braves beat Boston 4-2 behind seven one-run innings thrown by Sale.

It's also worth noting that one player who's now on the Brewers was a part of those games last year as a member of the Red Sox. Infielder David Hamilton, who was traded to Milwaukee in the Caleb Durbin deal this past offseason, was used as a pinch runner by Boston in both contests. When MLB.com's Adam McCalvy recently pointed this out to Hamilton, the speedster said "lucky us."

Some Brewers fans might not be too excited about being on the opposite side of these two pitching matchups. But since the Red Sox went 0-2 when they faced reigning Cy Young Award winners in back-to-back games, Milwaukee has the chance to make its own history by defeating Skubal and Skenes.