5 Can’t-Miss Pitching Matchups This Week (Sept 30– Oct 5th, 2025)

The postseason has arrived and pitching arms better be ready. The Wild-Card series starts on September 30 and will bring

MLB: Boston Red Sox at Houston Astros
Troy Taormina-Imagn ImagesTroy Taormina-Imagn Images

The postseason has arrived and pitching arms better be ready. The Wild-Card series starts on September 30 and will bring with it all of October’s excitement and urgency into a short, do-or-die series.

That means every starter matters, and every outing can redefine the entire season. Here are five pitching matchups to watch for this week:

Tarik Skubal (Tigers) vs. Gavin Williams (Guardians) — Tuesday

MLB: Cleveland Guardians at Detroit Tigers
Credit: Rick Osentoski-Imagn Images

Skubal’s great season has him in the hunt for the Cy Young and he strats the series against divisional rival Cleveland. Across the way Williams has become the Guardians ace-in-the-making and brings upper-90s heat into his first postseason start.

It’s a pure AL Central clash: power vs. poise, both with lineups that know each other inside out.

Garrett Crochet (Red Sox) vs. Max Fried (Yankees) — Tuesday

MLB: New York Yankees at Boston Red Sox
Credit: Brian Fluharty-Imagn Images

Fenway and Yankee Stadium don’t need added drama but they’ll get it here. Garrett Crochet has been one of the American League’s most electric strikeout pitchers and Fried has big game experience and a steady left arm the Yankees want in October.

With Boston’s rotation thinned by Lucas Giolito’s late injury scratch the Red Sox are counting on Crochet to set the tone against their biggest rival.

Blake Snell (Dodgers) vs. Hunter Greene (Reds) — Tuesday

MLB: Philadelphia Phillies at Los Angeles Dodgers
Credit: Jayne Kamin-Oncea-Imagn Images

The defending Cy Young winner against Cincinnati’s triple-digit flamethrower ,  it’s as fun as it sounds. Blake Snell gives LA veteran stability in October while Greene brings pure and unfiltered velocity and strikeout power that can neutralize even the Dodgers’ loaded lineup.

Expect swings and misses galore with a playoff environment thick enough to cut with a knife.

Nick Pivetta (Padres) vs. Matthew Boyd (Cubs) — Tuesday

MLB: New York Mets at Chicago Cubs
Credit: Matt Marton-Imagn Images

Chicago turns to Matthew Boyd who earned the Game 1 start after one of the best seasons of his career. Across from him is Nick Pivetta the Padres’ late-summer workhorse whose swing-and-miss fastball has kept hitters guessing.

October Wrigley Field has its own mystique and this matchup is just another example of that with veteran arms and crowds on top of each other with everything on the line.

Yoshinobu Yamamoto (Dodgers) vs. Zack Littell (Reds) — Wednesday

MLB: Chicago Cubs at Cincinnati Reds
Credit: Aaron Doster-Imagn Images

If the series reaches a Game 2, it’ll also be a very good one. Yamamoto, the Dodgers’ significant offseason acquisition, has given them all they could hope for with a combination of command and strikeouts.

Littell on the other hand is a reliable innings-eater and that leaves the Los Angeles lineup in a steady state.

Also Read:: Top 5 Must-Watch MLB Games This Week (September 29– October 5th, 2025)

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Category: General Sports