Two MLB Playoff Bets Stand Out on Monday

Both American League Divisional Series continue on Monday as each series' favorite tries to climb out of a 1-0 hole.

In a late-afternoon showdown, the Chicago White Sox will try to continue their perfect postseason in Game 2 against the Cleveland Guardians after a 3-0 win to open the series powered by Munetaka Murakami’s two-run homer.

On Monday night, the New York Yankees send out their ace Cam Schlitter against the Tampa Bay Rays, who won their series opener 1-0 when Drew Rasmussen carried a no-hitter into the 8th inning.

Here are our best picks for Monday’s postseason action.

Chicago White Sox first 5 innings money line (+140, DraftKings)

At first glance, the Guardians appear to have the clear pitching advantage by sending out strikeout artist Gavin Williams to start Game 2.

But when you look at the matchups, that edge disappears.

The Guardians lineup is slashing just .190/.261/.222 against White Sox left-hander Anthony Kay. That is reflective of larger struggles against Southpaws: The Guardians had MLB’s fourth-worst OPS against left-handed pitching this season at .675.

Additionally, there’s still the potential for lingering rust for an offense that scored the fewest runs of any team to reach the 2026 postseason: This is just the Guardians’ second game since the end of the regular season more than a week ago.

With the White Sox possessing a less-than-exceptional bullpen, take the Southsiders through five innings rather than nine.

Tampa Bay Rays to win Game 2 (+114, FanDuel)

Yes, the Yankees will feel confident behind Schlitter, who is the overwhelming favorite to win the AL Cy Young this season. But the Rays are in an excellent position to counter him by committee after Rasmussen pitched eight innings in Game 1.

Rays relievers ranked just in the middle of the road in terms of ERA, but that was at least partly due to a fairly hefty workload well north of 600 innings this season. Their bullpen WHIP of 1.20 -- the third best in MLB and one spot ahead of the Yankees -- suggests an elite ability to mix and match when well rested.

Additionally, while starter Freddy Peralta has not been a mystery to the current Yankees lineup over the years, he has been exceptional in his last five starts, pitching to a 0.79 ERA.

And Tampa Bay has been very tough to beat at home in these teams’ season series: the Rays are now 6-2 against the Yankees in their eight meetings in 2026 at The Trop, including Saturday’s Game 1 win.

None of this is to say the Yankees won't win and send this series back to the Bronx knotted at 1-1. But if oddsmakers are giving you better than even money on the Rays money line, you should take it.