Chicago White Sox vs Boston Red Sox Prediction 4/21/25 MLB Picks

The Chicago White Sox and the Boston Red Sox meet Monday in MLB action from Fenway Park. We will look at this from a betting perspective and determine the best bets for this game. Here’s a Chicago White Sox vs. Boston Red Sox prediction.

Starting Pitching Matchup

The Chicago White Sox will send out Jonathan Cannon for the start here and Cannon is 0-2 with a 4.42 ERA and 18 strikeouts this season. This will be Cannon’s first career start against the Red Sox. The Boston Red Sox will trot out Walker Buehler for the start here and Buehler is 2-1 with a 5.23 ERA and 17 strikeouts this season. This will be Buehler’s first career start against the White Sox.

Chicago White Sox Recap

The Chicago White Sox come into this game looking to add on to their 8-4 win over the Red Sox from Sunday’s matchup to improve to 5-16 on the year. After this series, the White Sox will head on the road once again for a series against the Minnesota Twins.

White Sox Looking To Salvage Series Split

Lenyn Sosa leads the White Sox with 18 hits including a pair of doubles and 8 RBIs. Andrew Benintendi has 10 hits including 3 home runs, 7 RBIs and a .244 batting average while Miguel Vargas has a team-high 4 doubles and 6 RBIs. Brooks Baldwin has also added 9 RBIs while Luis Robert Jr. has a team-high 6 stolen bases so far this season. Nick Maton also has a pair of home runs for the White Sox while Andrew Vaughn has 2 home runs and 8 RBIs as well this season.

Why the Chicago White Sox will win

• The Red Sox have lost each of their last three games as favorites against the White Sox following a home loss.
• The White Sox have won nine of their last 12 games as road underdogs against the Red Sox following a win.
• The Red Sox have failed to cover the run line in each of their last six home games after playing the previous day.
• The White Sox have covered the run line in eight of their last nine day games following a win.

Chicago White Sox Player Prop Facts

• Luis Robert has hit at least one home run in five of his last eight appearances in day games against AL East teams that held a winning record.
• Luis Robert has scored at least one run in seven of his last eight appearances in day games against AL East teams that held a winning record.
• Andrew Vaughn has recorded at least one Single in five of the White Sox’s last six games against AL East opponents that held a winning record.
• Andrew Vaughn has recorded at least one hit in each of his last 10 Monday appearances with the White Sox as underdogs.
• Korey Lee has recorded at least one RBI in four of his last five appearances in day games against teams that held a winning record.
• Luis Robert ranks T5th in the league in Steals (7) this season.

Boston Red Sox Recap

The Boston Red Sox will try to rebound after their loss to the White Sox in Sunday’s matchup. After this series, the Red Sox will welcome the Seattle Mariners to town.

Red Sox Looking For Back-To-Back Series Wins

Trevor Story leads the Red Sox with 27 hits including a team-high 5 home runs and 14 RBIs along with a team-high 6 stolen bases. Alex Bregman has 25 hits with 7 doubles, 4 home runs and a team-high 16 RBIs while Jarren Duran has 21 hits with 4 doubles, a triple, a home run, 10 RBIs and 6 stolen bases of his own. Wilyer Abreu has 5 doubles, 3 home runs and 12 RBIs while Rafael Devers has 19 hits with 7 doubles of his own, 2 home runs and 12 RBIs but also has the dubious distinction of leading the Red Sox with 30 strikeouts so far this season.

Why the Boston Red Sox will win

• The White Sox have lost each of their last eight Monday road games against AL East opponents.
• The Red Sox have won seven of their last eight day games against AL Central opponents following a home loss.
• The White Sox have failed to cover the run line in each of their last eight Monday day games as road underdogs against American League opponents.
• The Red Sox have covered the run line in each of their last four games against AL Central opponents following a home loss.

Boston Red Sox Player Prop Facts

• Wilyer Abreu has hit a home run in each of his last two home appearances against the White Sox after playing the previous day.
• Walker Buehler has recorded a win in each of his last four appearances in day games against teams that held a losing record.
• Alex Bregman has scored at least one run in each of his last four appearances.
• Trevor Story has recorded at least one Single in each of his last nine appearances against AL Central opponents.
• Walker Buehler has recorded seven or more strikeouts in three of his last four home appearances against opponents that held a losing record.
• Trevor Story has recorded at least one hit in each of his last nine appearances against AL Central opponents.
• Connor Wong has recorded a Double in each of his last three appearances in day games against teams that held a losing record.
• Connor Wong has recorded an RBI in each of his last four appearances against AL Central opponents.

Total Runs Facts

• Five of the Red Sox’s last six home games after playing the previous day have gone UNDER the total runs line.
• Four of the White Sox’s last five day games against AL East opponents have gone UNDER the total runs line.

Chicago White Sox vs. Boston Red Sox Prediction

I’m on the over in this one. I get the case to be made for Boston but the Red Sox are such heavy favorites that it’s hard to find value with them and Buehler isn’t a pitcher I’m trying to lay big odds or a run line with. On the other side, I’m not sure sustained success and the Chicago White Sox are two things that will go hand in hand very often this season, but I think we have some runs lined up for Monday’s series finale. Give me the over here.

Chris Ruffolo's Pick: Over 9