White Sox Set Pitching Matchups for Season-Defining Guardians Series

It's the biggest series of the year for the Chicago White Sox, beginning Monday night in Cleveland. The fate of the AL Central, and potentially Chicago's entire season, hangs in the balance.

Just half a game separates the two teams in the standings with 13 games remaining in Chicago's regular season. The White Sox also have an opportunity to secure the season tiebreaker over the Guardians by winning just one game, giving them the head-to-head advantage. That could loom large over the final two weeks of the year.

The White Sox have talked about this series essentially serving as an early playoff series, and the Guardians are already treating it like one. Cleveland altered its starting rotation over the last few days to ensure it's putting its best foot forward against Chicago.

Gavin Williams has been one of Cleveland's premier starting pitchers in 2026, posting a 3.78 ERA with 228 strikeouts over 169 innings. Williams was scheduled to start for the Guardians over the weekend against the Minnesota Twins, but Cleveland instead pushed him back to take the ball Monday against the White Sox.

That gives the Guardians their three most promising starting pitchers for the series, with Williams on Monday followed by All-Star starters Foster Griffin and Parker Messick on Tuesday and Wednesday.

Here's a closer look at the upcoming series, the pitching matchups and who the White Sox will send to the mound as they attempt to regain some momentum and make a statement in the AL Central.

The White Sox will send Sean Newcomb to the mound as an opener Monday in Cleveland.

Newcomb has been a Swiss Army knife for the White Sox throughout 2026 and has a strong case for being the pitching staff's MVP this season. Will Venable has deployed him in high-leverage situations and as a multi-inning reliever. This time, Newcomb will get the ball as an opener, and the White Sox will likely try to get two, or perhaps even three, innings out of him.

Sean Burke was originally scheduled to start Monday, but after a disastrous outing against the Pittsburgh Pirates last week, the White Sox are trying something different. Burke will be the bulk reliever following Newcomb.

Williams has faced the White Sox three times in 2026, recording a 4.11 ERA in those starts. When he's on, he's one of the most overpowering starting pitchers in the American League. But Chicago's track record of success against Williams offers some hope for Monday night.

Davis Martin will take the ball for the White Sox on Tuesday as he looks to continue his success in September.

Martin has been a different pitcher since returning from the IL at the beginning of the month. He threw 5.2 scoreless innings against the Houston Astros before delivering five innings of one-run ball against the Pittsburgh Pirates.

Unfortunately, the White Sox failed to give Martin enough run support in either outing, wasting two strong starts in a pair of losses.

Martin, though, has faced Cleveland twice in 2026 and struggled both times. He completed just 4.1 innings across those two starts, allowing three earned runs, eight hits and six walks.

The White Sox will hope Martin can continue his recent success Tuesday. He may not be able to pitch deep into the game, but if he can provide five solid innings and give the offense an opportunity to pull away, Chicago should consider that a win from a pitching perspective.

His opponent will be Griffin, who was an All-Star with the Washington Nationals and went 12-3 with a 3.06 ERA in 22 starts before the trade deadline. Since being acquired by Cleveland, Griffin is 3-2 with a 5.94 ERA over seven starts and hasn't looked like the same pitcher.

Griffin did, however, face the White Sox earlier this season as a member of the Nationals. He delivered seven scoreless innings, allowing just two hits while striking out eight.

The Guardians will send All-Star left-hander Parker Messick to the mound for Wednesday's series finale.

Messick is 11-9 with a 2.51 ERA this season. In three outings against the White Sox, he's 1-1 with a 2.29 ERA over 19.2 innings.

It remains unclear who the White Sox will send to the mound.

Chicago realistically has two options. The White Sox could turn to Erick Fedde, perhaps following an opener, and allow the veteran to take the ball after a full week of rest. Fedde last pitched Thursday against the Pittsburgh Pirates, and it's hard to argue with the 1.50 ERA he's posted over his last five outings since moving back into a rotation role.

Fedde has faced Cleveland three times in 2026, with each appearance coming out of the bullpen and two coming as a bulk reliever following an opener. He has thrown 10.1 innings against the Guardians, going 1-0 with a 2.61 ERA.

But the White Sox still have a decision to make because Anthony Kay's numbers against Cleveland are even better, and the matchup could provide Chicago with a distinct advantage in the series finale.

Kay has faced Cleveland three times this season and is 1-0 with a 1.69 ERA, allowing just three earned runs over 16 innings. As a team, the Guardians have performed worse against left-handed pitching than right-handed pitching. They have a .659 OPS and just a .226 batting average against lefties this season.

That being said, Kay hasn't pitched well recently. He is 0-4 with a 6.83 ERA over his last six starts.

Do the White Sox ride the hot hand with Fedde, or do they play the matchup with Kay, a pitcher who has enjoyed considerable success against Cleveland this season? Kay would be pitching on normal rest if he takes the ball Wednesday.

That's the question still facing the White Sox ahead of the series, and the answer could make or break their season.

These might as well be playoff games for Chicago. The division could very well be won or lost over the next three days, and these pitching matchups will play a major role in deciding which team emerges with the advantage.