The Chicago White Sox head to Progressive Field on Wednesday, September 16, 2026 for a 1:10 PM ET matinee against the Cleveland Guardians. Anthony Kay gets the ball for Chicago against Cleveland's Parker Messick in what shapes up as a pitching matchup between two arms the Sox will need to lean on down the stretch of the regular season. The game airs nationally on ESPN and ESPN App, so the South Siders will have a wide audience watching every inning.

Pitching Matchup: Anthony Kay vs. Parker Messick

Anthony Kay draws the start for the White Sox. Kay has been part of a rotation that has had to grind through a long regular season, and Wednesday's outing in Cleveland is another audition — both for his own future with this club and for a team still defining what it wants to be. There is no sugarcoating it: detailed ERA and win-loss data wasn't available at time of publication, so we'll let his performance on the mound do the talking.

On the other side, Parker Messick takes the hill for the Guardians. Messick is a left-handed presence Cleveland has been developing, and he presents a challenge the Sox offense will need to solve early. Same story on the stats front — watch the first two innings to gauge what his stuff looks like on the day.

Cleveland Guardians Lineup to Watch

Cleveland is sending out a formidable order. José Ramírez hits second and remains the gravitational center of this offense — he is the player the White Sox absolutely cannot let beat them with runners on base. Steven Kwan leads off and brings a disciplined at-bat that can grind Kay's pitch count up in a hurry. Jo Adell slots in at third, giving Cleveland a power threat in the middle of the order, while rookie Travis Bazzana bats cleanup at DH.

• Steven Kwan (LF, leadoff): A contact-first hitter who makes pitchers work and sets the table for what follows.
• José Ramírez (3B, 2-hole): The most dangerous hitter in this lineup. Kay must limit his damage with runners on base.
• Jo Adell (RF, 3-hole): Power threat capable of changing the game with one swing.
• Travis Bazzana (DH, cleanup): The young Cleveland first-rounder brings upside that makes this lineup even more difficult to navigate.

Keys to the Game for the White Sox

• Kay's command early: If he falls behind in counts against Kwan and Ramírez, this game can get expensive fast. Throwing first-pitch strikes is non-negotiable.
• Neutralize Ramírez: This is the same bullet point every time the Sox face Cleveland, and it never stops being true. Keep him off the bases.
• Bullpen management: With no publicly available data on Kay's current workload, the White Sox coaching staff will need to read his stuff in real time and not let a struggling Kay linger too long.
• Capitalize on Messick early: If the Sox can get to Messick in the first two innings before he finds a rhythm, they take pressure off their own pitching staff.

Prediction

This is a tough road spot. Progressive Field is a hostile environment late in the season, Cleveland's lineup is built to punish mistake pitches, and the White Sox are asking Kay to keep them in a game against a quality opponent. Cleveland's lineup depth — from Kwan at the top through Bazzana in the cleanup spot — gives the Guardians the edge here. Expect a competitive game, but the home side has the advantage. Guardians 5, White Sox 3.