In 2025, the Cleveland Guardians made one of the most stunning rallies in MLB history, as they were 11 games behind the Detroit Tigers in early September before going on to win the AL Central. This season, it’s been much of the same; Cleveland was six games behind the Chicago White Sox in mid-August, but it claimed the final two games of their series last week to open up a one-game lead.
The Guardians are in for a test this week in the form of a three-game road series against the Boston Red Sox at Fenway Park. The Red Sox are locked into a Wild Card spot, although they could still technically have home-field advantage against the New York Yankees.
Tonight’s series opener is scheduled to begin at 6:45 p.m. ET. Parker Messick will take the mound for Cleveland, and Payton Tolle will start for Boston.
Let’s break down this potential playoff preview with some odds and lines at DraftKings Sportsbook.
Cleveland Guardians at Boston Red Sox Best Bets
- Cleveland Guardians Moneyline (+108): It’s hard to find much of a flaw with either of these starting pitchers, but given that Messick’s road ERA is 1.34 runs lower than Tolle’s home ERA and both bullpens have been spectacular, I’ll take the Guardians to just edge this one out.
- First 3 Innings Correct Score: 0-0 (+285): Messick has allowed just a .501 OPS the first time through the order, so I find it hard to believe that the hosts will score in the first three innings. Tolle has been slightly worse, but a .643 mark is still good enough to stymie a relatively soft-hitting Cleveland offense.
Cleveland Guardians at Boston Red Sox prediction, preview
The Guardians’ September in 2026 hasn’t been quite as hot as their September in 2025, but at 12-7, it certainly isn’t bad, especially given that they also won eight of their last 10 games in August. In fact, in the last 30 days, Cleveland has posted the league’s eighth-highest OPS, and José Ramírez has recorded four consecutive multi-hit games. Chase DeLauter and Travis Bazzana have also had tremendous rookie seasons, with Bazzana slashing .302/.403/.698 since the start of the month. Still, the Guardians’ offense can be merely league-average and still win games, as they’ve consistently had an above-average pitching staff. Cleveland’s starters had a sub-4 ERA in each of the first five months of the season before struggling to start September, and its bullpen has shut it down, pitching to a 2.29 mark so far this month. Gavin Williams leads the American League in strikeouts and Messick should receive some Cy Young Award consideration. Furthermore, five of the Guardians’ six relievers with at least 45 innings pitched this season have a sub-3 ERA, so as long as they enter the latter phases of the game with a lead, they should be in good position to hold on.
The Red Sox, on the other hand, have slowed down since a torrid 27-3 stretch in July and August, and they could lose the opportunity to pass the New York Yankees for the fourth seed with a defeat tonight, but a 9-9 record in September isn’t a disaster entering the postseason. What is more concerning is the fact that Boston ranks third-to-last in OPS over the last 30 days, as Adley Rutschmann — acquired at the trade deadline for a steep price — has just a .597 OPS in that stretch and both Willson Contreras and Ceddanne Rafaela have missed some time. The Red Sox could improve later this week now that Contreras is back and Rafaela is set to join him. In the meantime, Boston has been kept afloat by its pitching; its starters have posted a sub-4 ERA in each of the past five months, and its bullpen has recorded a sub-3 mark in May, July, and September. Sonny Gray and Tolle have formed a devastating 1-2 punch at the top of the rotation, with Garrett Whitlock, Alec Gamboa, and the ageless Aroldis Chapman holding it down with sub-2 marks in relief. It’s even possible that the Red Sox could add a Cy Young finalist to their bullpen for the playoffs, as Garrett Crochet (shoulder) hasn’t ruled out a return.
The fact that Messick could somehow finish higher in Cy Young rankings than Rookie of the Year rankings is a testament to how good his season has been. The southpaw has pitched into the sixth inning in 23 of his 30 starts, allowing two or fewer earned runs on 23 occasions and never allowing more than four earned runs in any start. In fact, he’s pitched to a 2.21 mark since the start of July. Advanced numbers paint an overwhelmingly positive picture of him; he ranks in the 87th percentile in xERA and the 98th in pitching run value, and he sits above the league median in every single Statcast category other than fastball velocity. He’s comparatively struggled to generate chases or whiffs, but Boston operates a pretty aggressive plate approach, mitigating that relative shortcoming. Messick has particularly excelled at inducing soft contact, ranking in the 78th percentile or better in average exit velocity, barrel rate, and hard-hit rate, exacerbating one of the Red Sox’s biggest weaknesses. To be fair, Boston has been significantly more effective at Fenway Park, but Messick has been nearly un-hittable on the road, posting a 2.21 mark on unfriendly turf.
It should be a proper pitcher’s duel between him and Tolle. Tolle, a fellow rookie southpaw, has recorded a 3.02 ERA in 25 starts, pitching into the sixth inning 18 times and allowing two or fewer earned runs on 18 occasions. After a shaky start on July 1 (three innings, six earned runs), Tolle has registered a 2.62 mark over his last 12 games, and the Red Sox have won 11 of those. Statcast likes him even more than Messick, as he sports a 96th-percentile xERA, 93rd-percentile xBA, and 90th-percentile pitching run value. Tolle also ranks in the top quintile in chase rate, strikeout rate, and walk rate, countering some of Cleveland’s biggest strengths. The 23-year-old’s biggest weakness is his propensity to give up fly balls (he ranks in just the 21st percentile in that stat), and while the Guardians have done an excellent job getting the ball in the air, they rank in the bottom five in all three slugging stats, and Tolle has been good at limiting hard contact as is. The location splits are mixed; although Cleveland’s offense has been worse on the road, Tolle’s ERA is 1.05 runs higher at hitter-friendly Fenway Park.
Cleveland Guardians at Boston Red Sox pick, best bet
Best Bet: Cleveland Guardians Moneyline (+108)
Although Boston has more raw talent in its lineup than the Guardians do, Cleveland has posted an OPS 67 points higher over the last 30 days, a not-insignificant margin. I like Messick on the road slightly more than Tolle at home.
Strong Lean: First 3 Innings Correct Score: 0-0 (+285)
Both of these pitchers have been spectacular the first time through the order, as Messick has limited opponents to just a .501 OPS and Tolle a .643 mark in that split. Both teams have a sOPS+ below 100 their first time facing a starter.
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