The Ludington football team has never won a playoff game in school history entering Friday, despite making the postseason three of the last four seasons.
Both teams failed to score during the first quarter.
The Orioles scored two touchdowns during the second quarter on a one-yard run by Stephen Weinert and a 13-yard pass from quarterback Brad Mesyar to Weinert.
John Glenn scored before the end of the first half, cutting its deficit to 12-7.
The score remained the same until 1:36 left in the contest as John Glenn scored a touchdown to take a 15-12 lead.
Ludington took the ensuing kickoff just past midfield, then scored with just over a minute left in the contest on a 13-yard completion from Weinert to Mesyar.
The Orioles forced John Glenn to turn the ball over on downs to seal their first ever playoff win.
Mesyar threw for 185 yards and two touchdowns while Weinert ran for 45 yards and a touchdown on the ground to go along with two receiving touchdowns.
Ludington was led defensively by Braden Chadwick with 11 tackles and a block punt, while Levi Laman and Jacob Irelan had nine and seven tackles, respectively.
The Orioles are now 5-2 on the season and will face the winner of Sault Ste. Marie and Saginaw Arthur Hill next week in the district semifinals.