Walk-Off Wagers: MLB Best Bets Today (Brewers Will Upset Cubs in Chicago)

Iain MacMillan | Aug 21, 2025

Bet the Brewers as road underdogs against the Cubs on Thursday. / David Banks-Imagn Images

We have a short slate of MLB games set to take place today as teams either wrap up their mid-week series or settle in for an extended series this weekend.

Even with just nine games scheduled for Thursday, we still have plenty of opportunities to try to win some bets. In today's edition of Walk-Off Wagers, there are two games I'm targeting as my best bets, including the Milwaukee Brewers to bounce back with an upset win against the Chicago Cubs. Let's dive into them.

Top MLB Picks Today

Odds via FanDuel Sportsbook

• Brewers +116 vs. Cubs
• Cardinals vs. Rays UNDER 8.5 (-115)

Brewers vs. Cubs Prediction

Due to a double-header on Tuesday, the Brewers and Cubs are wrapping up a rare five-game series this afternoon. The Cubs have already won the series, winning three straight, but can put a stamp on a pivotal series with another win this afternoon. Unfortunately for them, I think the Brewers are the side to back in this one.

Despite the last few days going in the Cubs' favor, you can't ignore how much better the Brewers' offense has been of late. Since the All-Star Break, the Brewers have an OPS of .823 and rank second in the Majors in wRC+. In that same time frame, the Cubs have an OPS of .669 while ranking 26th in wRC+.

Shota Imanaga gets the start for the Cubs today, but he's struggled when facing the Brewers this season. In two starts against them, he has allowed nine hits and five earned runs in 10.2 innings pitched.

For those reasons, I'm backing the Brewers as underdogs in this spot.

Pick: Brewers +116

Cardinals vs. Rays Prediction

The St. Louis Cardinals and Tampa Bay Rays have had two of the worst offenses in Major League Baseball since the All-Star Break, making the UNDER the obvious side to back when these two open an interleague series against each other tonight.

Since July's pause in play, the Cardinals rank 27th in wRC+ and the Rays rank last amongst all teams. Tampa Bay is also batting just .222 with an OPS of .655.

While neither starting pitcher in tonight's matchup is elite, Sonny Gray (4.30 ERA) and Joe Boyle (4.68 ERA) are both certainly good enough to keep the opposing struggling offenses in check. I'm surprised the total is set at 8.5 in this one. Give me the UNDER.

Pick: UNDER 8.5 (-115)

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You can check out all of Iain's bets here!