Ranking the 3 worst first-round playoff matchups White Sox should try to avoid

I know, I know. Talking about the playoffs right now is a bit difficult. The White Sox have successfully squandered their entire division lead in recent days and have played their worst stretch of baseball since the beginning of April, leaving the entire season in doubt. Fortunately, the math is still on their side. With Toronto and Texas unable to string together wins to this point and the White Sox owning the tiebreaker over both teams, their odds of making the playoffs in some capacity are still pretty high, even if they don’t end up winning the AL Central. With a lot up in the air when it comes to the division winners and seeding, the team’s first-round opponent should they make it is still unclear. Here are the three matchups the White Sox would do best to avoid in the postseason. 

3) Hosting the Toronto Blue Jays 

The White Sox have the tiebreaker over Toronto after finishing 5-1 against them this season, so although it’s a team they’ve played well against, it’s not a matchup I love in a Postseason series. The Blue Jays have AL Cy Young candidate Dylan Cease to anchor their rotation and a team full of players who are hungry after coming one run short of winning the World Series in 2025. It’s an aging core and a team that’s struggled to put together consistent wins all season long, but it’s a team with experience winning on the biggest stage possible, and I’ll certainly be wary of that. Compared to some of the other possible first round matchups, this isn’t the worst-case scenario, but you can’t simply look at how well the White Sox have played Toronto this year and assume it’ll be an easy win either. On the bright side, if the White Sox play Toronto in the playoffs, it’ll almost certainly be with home-field advantage in the series. 

2) A division date with the Cleveland Guardians 

There is a very realistic scenario in which the White Sox and Guardians series beginning Monday in Cleveland is not the last time the two teams face each other this year. With Cleveland and the White Sox both in the mix for the AL’s second and third seeds, as well as the third wild card, the door is open for a scenario where the White Sox head to Cleveland or vice versa. The White Sox enter Monday’s series opener with a 6-4 record against Cleveland this year, so they’ve held their own, but pitching often prevails in the Postseason, and I’d definitely give the edge to the Guardians in the starting department. Righty Gavin Williams and rookie lefty Parker Messick have dominated hitters all season, and each have had good outings against the White Sox already this year. A short series where the White Sox have to face both pitchers would be an incredibly tough task for a young lineup. 

1) Heading to Houston 

The last time the White Sox made the playoffs, they were defeated handily by the Houston Astros in the ALDS. That was, of course, a very different Astros team and a very different playoff structure, but Houston remains one of the more consistent winning organizations in baseball. Even in a down year by their standards, the Astros have outplayed the White Sox substantially during their seven meetings, with the White Sox salvaging just two of the games. Houston righty Hunter Brown has had the White Sox’ number in both outings against them, and the Astros lineup features likely AL MVP Yordan Alvarez as well as a crew of guys that’ll make you pay for mistake pitches. Something about baseball in October makes the Astros take their game to another level, and I’d like to avoid playing them at all costs if I were the White Sox. I’d give the White Sox a better chance to win that series at home vs. having to head to Houston, but it’s still a team I want no part of in October.

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