The White Sox have tied the American League record for most consecutive losses in a single season, losing their 21st in a row on Monday. They share the record with the Orioles, who lost 21 straight in 1988 — a year in which Baltimore went 54-107.
With 47 games left in their season, the White Sox would need a significant shift to match Baltimore’s 1988 finish. Sitting with a .235 winning percentage at 27-88 entering Tuesday’s matchup, their pursuit of the modern era’s worst record in a 162-game season appears more likely. And that modern-era record isn’t the only one Chicago could break this season.
The 1961 Phillies hold the modern-era record for most losses in a row with 23. All-time, the 1889 Louisville Cardinals hold the record with 26 consecutive losses. DraftKings Sportsbook bettors can now back the White Sox to surpass one or both of those numbers — or even come up short.
On DraftKings Sportsbook, there is now a “WHITE SOX” market in the MLB section that allows bettors to bet on how much longer Chicago’s losing streak will last. Entering Tuesday’s contest vs. Oakland, who defeated the White Sox 5-1 on Monday, bettors can take the over or under on any total from 22.5 to 27.5:

The White Sox are +170 underdogs in Oakland on Tuesday, while the A’s are -205 favorites. With Jonathan Cannon on the bump for Chicago, an upset could happen. However, even with the promise the rookie has shown, the White Sox are 4-9 in his starts. Oakland has also flashed some power against right-handed pitching, posting an MLB-best .225 ISO against them in July.
With the over on each total in the WHITE SOX market at plus-money, it’s easier to go the conservative route. Splitting a unit is also an option. Backing the over on 22.5 at +145 could serve as an anchor, with that taking Chicago through Oakland.
From there, the White Sox face the Cubs for two games before hosting the Yankees. No one wants to be the team that the White Sox end their streak on, least of all the Cubs. So, betting the streak to go over 24.5 (+475) rather than 23.5 (+310) is a way to secure more value.
From there, the Yankees should sweep the White Sox — but it’s elite teams like New York who can somehow slip up against a bad team at their low point. That’s not to say this streak won’t extend vs. the Yankees. It just might be best to reach for over 25.5 (+600) at the most rather than over 26.5 or 27.5.
Simply use the search bar in the DraftKings Sportsbook app and type in “White Sox” to find the market to make your pick!
Place your bets at DraftKings Sportsbook or by downloading the DraftKings Sportsbook app.
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All odds provided by DraftKings Sportsbook and all odds subject to change.
All views expressed are my own. I am an employee of DraftKings and am ineligible to play in public DFS or DKSB contests.