MLB · 2 weeks ago

MLB Best Bets Today: Wednesday’s Top 2 Betting Picks (August 20)

Gabriel Santiago

Host · Writer

MLB Best Bets Today: Wednesday’s Top 2 Betting Picks (August 20)

There is no stopping us now. The MLB season and summer are fully underway, meaning there are betting opportunities every day between now and October. We’ve got you covered for Wednesday’s baseball schedule!

Where to Watch New York Yankees vs. Tampa Bay Rays

Ballpark: George M. Steinbrenner Field
Location: Tampa, FL
Where to Watch: YES, FDSNSUN
Time: 7:35 p.m. ET
Spread: NYY -1.5 (+164) | Total: 8.5 (-118/-104)
Moneyline: NYY +100 | TB -118

The New York Yankees will be in another one of those weird home-away games against the Tampa Bay Rays. George M. Steinbrenner Field may be where the Rays have set up shop in 2025, but it is still the long-time Spring Training home of the Bronx Bombers.

For Tuesday, the projected starters in West Central Florida will be right-handers Drew Rasmussen and Cam Schlittler. Rasmussen is having his best MLB campaign to date behind a 0.97 WHIP. Meanwhile, the rookie Schlittler has struck out 9.1 hitters per nine innings over six appearances.

The Rays may hold the pitching advantage here, but the Yankees boast a lineup that has built a .784 OPS this season, which is currently the best mark in baseball. Most folks who follow the game are well aware of how explosive this Bombers team can be. Across the way, Tampa is sporting a .710 team OPS.

The Yanks and Rays have already met in a dozen head-to-head contests this year. Throughout that batch, New York has gone 8-4 straight up; that includes a 4-1 record when competing in Tampa.

In a Yankee-friendly environment, I love New York’s even-money ML price at FanDuel Sportsbook.

Best Bet: Yankees ML (+100)

Where to Watch Milwaukee Brewers vs. Chicago Cubs

Ballpark: Wrigley Field
Location: Chicago, IL
Where to Watch: FDSNWI, MARQ
Time: 8:05 p.m. ET
Spread: MIL -1.5 (+164) | Total: 6.5 (-122/+100)
Moneyline: MIL -116 | CHC -102

For the final night game of 2025 between the Milwaukee Brewers and Chicago Cubs, we should see a fierce pitcher’s duel a la RHPs Jacob Misiorowski and Colin Rea. Get ready for another fun one from the “Friendly Confines."

Misiorsowski has dazzled in eight starts as a rookie, compiling a 3.29 FIP while punching out 12.98 batters per nine innings. Still, Rea has also been solid since coming to the Cubbies from this same Brewers team. In 2025, Rea shows a 3.99 ERA and 1.28 WHIP after 25 appearances.

At this juncture, it still feels unwise to rely on any over bets on Chicago. In nine of the past 10 games involving the Cubs, the under has cashed. Their hitting has improved over the past two nights, but Chicago will have its collective hands full taking on Misiorowski. Additionally, the Brewers’ lineup finally cooled off last night; Milwaukee was held to just one run in Tuesday’s nightcap.

In an attempt to squeeze one more day of profit out of the Cubs’ offensive woes (they are hitting just .181 (.527 OPS) over the past seven days), I am on under 6.5 tonight at Wrigley.