Only four MLB games are on tap for Monday, September 26, but this divisional duel in Boston is getting a lot of attention, so make sure you don’t miss out on the best Orioles vs. Red Sox betting pick and odds.

Baltimore and Boston will play the first of a four-game series at Fenway Park, and the Red Sox are -135 moneyline favorites on MyBookie Sportsbook, while the total is set at 9.5 runs. These AL East rivals have met 15 times this year, and the Orioles lead 8-7.

Orioles closed the series with the Astros with a loss

The Baltimore Orioles opened the home series against the Houston Astros with a couple of impressive wins in which they scored eight and allowed zero runs! Still, the Astros bounced back and won the next two games, including Game 4 in extra innings. Baltimore now dropped to a 79-73 record and is four wins behind the Seattle Mariners in a wildcard race.

It was a tied Game 4 until the 11th inning when the Astros scored four runs, and the Orioles managed to respond with just one, not enough to avoid a 6-3 defeat. Rougned Odor was a bright spot in Baltimore’s offense with two RBIs. Keegan Akin (3-3) took a loss, while starter Austin Voth (5-3) pitched well; he allowed one run on four hits with six strikeouts and no walks over 5.0 innings.

Jordan Lyles is getting his 31st start of the year when he takes on the Red Sox on Monday. The 31-year-old right-hander has a 4.50 ERA, 1.39 WHIP, and 135/50 K/BB ratio over 170.0 innings of work.

Red Sox are on a losing streak

The Boston Red Sox are in jeopardy of being swept by the arch-rivals New York Yankees on the road, as Game 4 of that series will be played on Sunday night. While we don’t know what’ll happen there, we do know that the Red Sox lost four consecutive games and 11 of the last 16. It was a disappointing campaign for Boston and will end it with a below .500 record.

Boston’s pitching staff didn’t play well in the most recent 7-5 loss to the Yankees. Starter Nick Pivetta (10-11) surrendered five runs on six hits with eight strikeouts and four walks in 5.0 innings in a no-decision. Reliever John Schreiber (3-4) took a loss. Triston Casas had the best game of his young MLB career as he chipped in three RBIs and also scored a run.

Connor Seabold (0-3) will get on the bump for the 5th time this year when he meets the Orioles on Monday. The 26-year-old right-hander is still looking for his first major league win in his 6th career start, but after pitching for 16.1 innings this season, Seabold owns a disastrous 10.47 ERA, 2.20 WHIP, and 17/6 K/BB ratio.



  • 4-0 in the last four games vs. a right-handed starter
  • 5-2 in the last seven road games
  • 14-6 in the last 20 during game 1 of a series


  • 0-4 in the last four overall
  • 0-5 in the last five games vs. a right-handed starter
  • 17-41 in the last 58 vs. American League East rivals

Baltimore Orioles vs. Boston Red Sox Pick

Connor Seabold allowed 4+ runs in three of his four starts this season and considering how good the Orioles are playing on the road and against right-handers of late, I don’t think he will enjoy a quality start on Monday. On the other side, Jordan Lyles had the second complete game of his 11-year career, the first since 2012, and signed a new one-year $7 million contract with the Orioles, so I expect him to be fired up in this one. The Orioles are 4-0 in Lyles’ last four starts with four days of rest, which is another reason I am backing the visitors here.

Pick: Take the Orioles to win (+115)

The Total

Although Lyles was impressive in his last outing, we cannot ignore the fact that he has an 8.00 ERA in 18.00 innings in four starts (1-1) against the Red Sox this season. He surrendered even eight runs in just 3.2 innings of work in his latest start against Boston, and even though I don’t expect him to melt down this time around, I am still backing the hosts to score multiple runs off of Lyles. Over is 3-0-1 in Lyles’ last four starts with the total set at 9.0-10.5, while Over is 4-0 in Lyles’ previous four starts vs. a team with a losing record.Pick: Go Over 9.5 runs (-110)