White Sox vs. Guardians ALDS 2026: First Series Win Since 2005

The Chicago White Sox closed out their Wild Card Series against the Houston Astros with a 7-3 win in Game 2, and per Bleacher Report, that sweep marked the first time since the 2005 World Series that the White Sox won a postseason series. Twenty one years without a series win is now over, against the AL West champion.

White Sox Guardians ALDS 2026: The Drought Is Over

The reward for Chicago's sweep is a trip to Cleveland. The White Sox vs. Guardians ALDS opens Saturday, Oct. 3, at 1 p.m. ET at Progressive Field, with the broadcast split across TBS, truTV and HBO Max, per MLB.com. Cleveland won the AL Central by finishing 85-77 to Chicago's 84-78, a one game margin that sent the White Sox into the Wild Card round instead of hosting a series of their own.

How Chicago and Cleveland Stack Up Head to Head

The two AL Central rivals split a tight regular season series, with the White Sox taking it 7-6 while outscoring the Guardians 58-57 across the 13 meetings, per MLB.com. Eleven of those 13 games were decided by three runs or fewer, and four went to walk-offs, a pace that suggests the ALDS won't look much different.

The most recent sample came in September, when the two teams played a series in Cleveland. The Guardians took two of three in that set despite the White Sox scoring 16 runs across the three games, per Bleacher Report. That is the same formula Chicago will need to flip starting Saturday: score in bunches and hope the pitching holds.

Chicago arrives with real offensive momentum. The White Sox scored 41 runs in the final week of the regular season and have put up 73 runs over their last 11 games dating back to a series against Detroit that began Sept. 18, per Bleacher Report. The lineup backed that up against Houston, piling up 13 runs over the two Wild Card games without needing one player to carry it. Chase Meidroth had multi-hit games in both wins and added a three run homer in the clincher, Braden Montgomery had two hits in Game 1 and Colson Montgomery went deep in the series opener, all per Bleacher Report.

Starting Pitching Still Unsettled

Neither team had locked in a Game 1 starter, per MLB.com. Cleveland was choosing between Gavin Williams and Parker Messick, its top two arms, while Bleacher Report's Wednesday preview projected a three man playoff rotation of Williams, Messick and Foster Griffin, with Tanner Bibee or Joey Cantillo in reserve for a potential Game 4.

Williams carries real swing and miss stuff, striking out 248 batters in the regular season with nine or more strikeouts in five of his last nine starts, per Bleacher Report. But he has not solved this particular opponent: Cleveland is 1-3 in his four regular season starts against the White Sox, even though he allowed three earned runs or fewer in every one of those losses. Messick has been more consistent against Chicago specifically, striking out at least eight in three of his four meetings with the White Sox and not allowing more than three earned runs in a start since June 29, per Bleacher Report.

For the White Sox, MLB.com listed Davis Martin, Anthony Kay and Erick Fedde as Game 1 candidates, and noted Chicago used an opener 31 times during the regular season, so a traditional announced starter is not guaranteed even once the decision is made.

Betting Impact: FanDuel Has Cleveland Favored

FanDuel Sportsbook priced Cleveland as a -168 Game 1 favorite (bet $168 to win $100) with the White Sox at +142 (bet $100 to win $142), and set the total at 7.5, according to Bleacher Report's odds published Wednesday, Sept. 30. That price reflects Cleveland's edge in starting pitching and bullpen depth, where Cade Smith headlines a group Bleacher Report called an advantage for the Guardians.

The number worth watching is Williams' Game 1 strikeout prop if Cleveland does start him. His 1-3 record against Chicago despite limiting earned runs suggests the White Sox lineup can scuffle against him without actually beating him on the scoreboard, a split that matters more for first five or team total unders than for the Williams moneyline itself. On the other side, Chicago's bottom of the order bats, Meidroth, Braden Montgomery and Colson Montgomery, are the names to track in DFS builds given their production in the Wild Card round, especially if the lineup card keeps them anywhere near their Houston spots.

Steven Kwan is the other name to know. He has hit .353 since the All-Star break, per MLB.com, and figures to be a lead off prop and total bases consideration all series if Cleveland's offense needs a jolt against a White Sox staff that is leaning on bullpen games.

What to Watch Next

The first marker is the Game 1 lineup cards and starter announcements, expected to firm up as Saturday's first pitch approaches. The second is whether Colin Holderman and Rhys Hoskins, both nursing injuries from late in the Guardians' regular season per MLB.com, are available in relief or off the bench once the series starts. The third is whether Chicago's bottom order production carries over from Houston, since that is the swing factor Bleacher Report flagged for the White Sox to push the series to five games.

For the rest of the bracket and where the lines are moving elsewhere, check the MLB daily picks board or the AI sports picks hub. We broke down how Cleveland got here in our piece on the Guardians clinching the AL Central, and Chad is already tracking Game 1 prop movement as both rotations firm up.

FAQ

When is White Sox vs. Guardians ALDS Game 1? Game 1 is Saturday, Oct. 3, at 1 p.m. ET at Progressive Field in Cleveland, broadcasting on TBS, truTV and HBO Max, per MLB.com.

When did the White Sox last win a playoff series before 2026? The 2005 World Series. Bleacher Report's ALDS preview said the Wild Card sweep of Houston was the first time since then that Chicago won a postseason series.

Who is favored in the White Sox-Guardians ALDS? FanDuel Sportsbook had Cleveland at -168 and the White Sox at +142 for Game 1, with a 7.5 total, per Bleacher Report's Wednesday, Sept. 30 odds post.

Who are the probable Game 1 starters? Undecided as of this writing. MLB.com had Cleveland choosing between Gavin Williams and Parker Messick, while Chicago's candidates included Davis Martin, Anthony Kay and Erick Fedde, with openers also in play.

Chad AI tracks every ALDS prop on this slate, from Williams' strikeout total to the Chicago bottom order bats, inside the StatSniper app.

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