Football Recap: Middletown's Run of Five Straight Wins Now Over + How To Watch

It's hard to turn regular season success into postseason wins, a fact Middletown can now relate to. They took a 28-21 hit to the loss column at the hands of the Monroe-Woodbury Crusaders on Saturday. While losing is never fun, the Middie Bears can't take it too hard given the team's big disadvantage in MaxPreps' New York football rankings (they are ranked 115th, while the Crusaders are ranked 18th).

Ayden Nauta threw for 68 yards. Aiden Barbosa was his top target, picking up 38 receiving yards and one TD. On the ground, Ryan Guevara rushed for 45 yards.

ETHAN MALDONADO produced another solid effort throwing for 226 yards and three touchdowns while completing 77.8% of his passes, and also rushing for 38 yards and one score for Monroe-Woodbury. That's the most passing yards MALDONADO has posted since back in October of 2024. A healthy portion of MALDONADO's aerial production (89 yards to be exact) went to BRAYLON SHILLINGFORD, who also brought in two receiving touchdowns.

Middie Bears

Previous 5 Games

11/15/25 vs Monroe-Woodbury	21-28
11/07/25 @ Newburgh Free Academy	21-16
10/31/25 vs Kingston	26-12
10/24/25 vs Our Lady of Lourdes	40-34
10/17/25 @ Valley Central	36-14

Middletown moved to 6-5 with that defeat, which also ended their five-game winning streak. As for Monroe-Woodbury, the victory was the tenth in a row for them, bringing their record up to 10-1.

Middletown does not have any more games scheduled as of now. As for Monroe-Woodbury, they will take on Mamaroneck at 3:00 p.m. on Saturday. The Tigers will aim to continue their three-game streak of scoring more points each game than the last.