PORTLAND, Maine – The Portland Sea Dogs, the Double-A affiliate of the Boston Red Sox, defeated the Chesapeake Baysox, the Double-A affiliate of the Baltimore Orioles, in back-to-back walk-off games on May 10 and 11, 2025, at Delta Dental Park. Portland won 4-3 on Saturday via a ninth-inning homer and 6-5 in 10 innings on Sunday with a two-run single, improving to 18-12. The losses dropped Chesapeake to 16-16, concluding their 12-game road trip.
On Saturday, Portland took a 1-0 lead before Chesapeake surged ahead in the sixth. Jeremiah Jackson’s two-run homer off Tyler Uberstine, his third of the season, gave the Baysox a 2-1 advantage. Portland’s Caden Rose tied the game with a leadoff homer in the sixth off Levi Wells, who earned a no-decision in his first career quality start, pitching six innings and allowing two runs on three hits. Hudson Haskin’s RBI single in the seventh put Chesapeake up 3-2, but Ahbram Liendo’s two-out RBI single in the eighth off Ben Vespi tied the game. In the ninth, Jhostynxon Garcia’s leadoff homer against Juan De Los Santos secured Portland’s 4-3 victory, snapping Chesapeake’s five-game win streak.
Sunday’s game extended to extra innings. Frederick Bencosme’s solo homer in the fourth gave Chesapeake a 1-0 lead, but Portland exploded for four runs in the bottom half off Braxton Bragg, with Blaze Jordan’s two-run single and Drew Ehrhard’s two-run double. The Baysox responded in the fifth, scoring twice via Jalen Vasquez’s fielder’s choice and Bencosme’s RBI single, trailing 4-3. Max Wagner’s eighth-inning double scored Jackson to tie the game at 4-4. In the 10th, Silas Ardoin’s double scored automatic runner Tavian Josenberger, giving Chesapeake a 5-4 lead. Portland countered in the bottom half, with Max Ferguson’s bunt single and Garcia’s two-run single scoring Liendo and Ferguson for a 6-5 win.
Wells pitched six innings Saturday, allowing two runs with two strikeouts, while Bragg threw four innings Sunday, surrendering four runs (one earned) with eight strikeouts. Connelly Early earned the win Sunday (2-0, 2.41 ERA), pitching five innings, while Keagan Gillies took the loss (2-1, 1.23 ERA). Jackson led Chesapeake with three hits across both games, including a homer and double, while Bencosme had three hits, including a homer. Garcia’s four RBIs across the games paced Portland.
Chesapeake struggled with runners in scoring position, going 3-for-12 Saturday and 3-for-14 Sunday, while Portland was 4-for-8 Sunday. The Baysox committed one error Sunday, and Portland played error-free both days. Saturday’s game, originally a doubleheader, was reduced to a single nine-inning contest due to weather, attended by an unspecified crowd. Sunday’s game drew 6,032 fans under sunny 56-degree conditions, lasting 2 hours and 41 minutes.
The Baysox return home to face the Akron RubberDucks on May 13 at 6:05 p.m., aiming to rebound from the sweep. Portland’s consecutive walk-offs highlight their clutch hitting, while Chesapeake’s offense showed resilience despite bullpen struggles in late innings.
