Blue Jays vs Red Sox Picks and Predictions: Toronto Opens Series in Boston With a Win

After winning three of four against the Yanks, Toronto opens up a new series against another AL East rival when it visits Boston. Find out what team we think will draw blood first in our MLB betting picks and predictions for Blue Jays vs. Red Sox.

Last Updated: Aug 23, 2022 11:14 AM ET Read Time: 4 min
George Springer Toronto Blue Jays MLB
Photo By - USA TODAY Sports

Following a day off yesterday, the Toronto Blue Jays will be looking to put more pressure on the falling Yankees tonight with a win against the Boston Red Sox.

Toronto enters the series opener as -140 road favorites with a big advantage in starting pitching, but the weather is also an issue that bettors should be paying attention to before getting down. Find out where my best bet lies in my free MLB betting picks and predictions for Blue Jays vs. Red Sox. 

Blue Jays vs Red Sox odds

This odds widget represents the best odds available for each betting market from regulated sportsbooks.

This moneyline saw plenty of action over a small amount of time this morning. Toronto opened at -135, then moved immediately to -175 before getting smashed back to -140 around 9 a.m. ET. Some books opened this total at 10 but the number has settled to a consensus 9.5.

Use the live odds widget above to track any future line movements right up until first pitch and be sure to check out the full MLB odds before placing your bets.

Blue Jays vs Red Sox predictions

Picks made on 8/23/2022 at 9:00 a.m. ET.
Click on each pick to jump to the full analysis.

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Blue Jays vs Red Sox game info

Location: Fenway Park, Boston, MA
Date: Tuesday, August 23, 2022
First pitch: 7:10 p.m. ET
TV: Sportsnet, NESN

Blue Jays vs Red Sox betting preview

Starting pitchers

Ross Stripling (5-3, 2.93 ERA): Stripling will be making his second start since a short injury-list stint but looked dominant in his first game back. He threw six perfect innings vs. Baltimore before giving up a couple of hits in the seventh inning. Stripling has seen the Red Sox twice this season and has allowed three earned runs over 10 innings. With the bullpen getting some rest, I doubt Stripling has a long leash today.

Josh Winckowski (5-6, 5.19 ERA): Winckowski just got the call from Triple-A to start today thanks to an injury to Nathan Eovaldi. The 24-year-old rookie was hit hard by the Pirates in his last start (six earned runs) which prompted the demotion. Over his 12 starts this season, the right-hander owns a 5.19 ERA, 1.50 WHIP, and a 36/21 K/BB ratio over 60-plus innings. Opponents are slashing a robust .291/.348/.486 and have launched 10 homers off him.



Be sure to monitor the gametime conditions with our MLB weather info.

Key injuries

Find our latest MLB injury reports.

Betting trend to know

The Blue Jays are 5-0 SU in the last five meetings in Boston. Find more MLB betting trends for Blue Jays vs. Red Sox

Blue Jays vs Red Sox picks and predictions

Our side and total predictions are based upon our analysis of the line and total in this game. Our best bet is our favorite pick across all markets.

Moneyline analysis

The Jays and Ross Stripling are gaining some steam in the market but today’s game is possibly offering some other factors that might not be priced in.

There is a serious rain concern tonight. Slow-moving storms are forecasted and the chance that there's a delay tonight is highly probable.

Playing in wet conditions will favor Stripling more than Boston starter Josh Winckowski. Stripling is an elite command pitcher with a walk rate that sits in the Top 4% of the league — which is in stark comparison to Winckowksi who has 21 walks in 60-plus innings. 

Winckowski doesn’t strike out batters (13.5% strikeout rate), gives up hard contact at a 30% rate, has a 0.915 OPS against at Fenway, and could be facing a stronger Toronto lineup that should feature George Springer in the leadoff spot. Springer had a day off yesterday which helped the veteran center fielder who was healthy enough to pinch hit Sunday, so a return today would make sense.

Stripling will face a Boston lineup that isn’t at 100%. Xander Bogaerts is dealing with shoulder pain from a late-May incident and although he is hitting .286 since then, he has just six long balls and can opt out to be a free agent this summer, so pushing it might not be in the cards. 

Tommy Pham is dealing with lower back tightness and Eric Hosmer is questionable (back), as well. Trevor Story is also on the IL. 

Toronto could be rolling at full strength offensively, while the Red Sox have plenty of moving pieces thanks to injuries, and their bottom third is hitting under .200 combined. 

With his command and experience, Stripling should be less affected by the likely rain than a rookie right-hander who struggles with command and gets hit hard at home. 

PredictionBlue Jays moneyline (-140 at bet365)

Over/Under analysis

The Jays have seen a total of 9.5 or higher just once since July 28 and that was a Yusei Kikuchi start. Stripling looked like his glute injury wasn't an issue in his last start where he was near perfect against the Orioles. The bullpen will also be rested and set for today with the day off yesterday. 

Interim manager John Scheider hasn’t given Stripling a long leash (pitch count) so having an available bullpen for the Toronto starter favors the Under here.

The Red Sox are also dealing with a weaker lineup as three possible starters (Boegarts, Pham, and Hosmer) are all playing at less than 100%. Their offense has also mimicked its playoff chances as this once Top 10 unit has been a Bottom 10 team in run production over the last 30 days. Only the Tigers have hit fewer home runs than Boston over the last month.

The Jays’ lineup has shown flashes of their early-season form thanks to Springer producing the gas, but any Jays fan knows that this lineup has struggled to produce runs over the summer months. Bo Bichette has dropped to the lower third of the lineup and having Jackie Bradley Jr. in the lineup helps the Under with his poor at bats but solid play in the field.

If this game sees a rain delay, we could also see both managers pull their less-than 100% hitters with a long playoff hunt in mind. 

PredictionUnder 9.5 (-110 at bet365)

Best bet

Winckowksi has walked 8% of the batters he’s seen which also works out to a 3.12 BB/9. He’s had multiple walks in just five of his 12 starts this season but THE BAT projects him for 88 pitches and his strike-looking percentage (19%) is unsustainable.

The right-hander sits in the Bottom 1% in K% and in the Bottom 4% in Whiff rate. Add in the potential for wet conditions, and the Jays could be seeing plenty of pitches from the rookie which increases his chances of walks. 

Winckowski is also not a traditional fastball pitcher and relies on his two best offerings (sinker/slider) which could also be affected by the pitching conditions. 

Josh Winckowksi Prop Pick: Over 1.5 walks (+120 at bet365)


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