The Pirates were up for the challenge when they took on No. 2 ranked Kentucky Country Day last month at home.
Berea Community took advantage of an early turnover to jump in front of the undefeated Bearcats (10-0).
"That lead held up until almost halftime," Berea Community coach Aaron Stepp said.
KCD went in front with 3:46 left before the half and pulled away for a 36-14 win at Duerson Stadium.
The Pirates (7-3) will get another shot at the Bearcats today in the opening round of the Class A Playoffs.
Kick-off is scheduled for 7:30 p.m. in Louisville.
The winner advances to play either Frankfort or Eminence next week in the district championship game.
Berea lost all three of its district games this season, but won every other game on the schedule.
The Pirates snapped a three-game losing streak with a 42-14 win over Jellico (Tenn.) last week at home.
Senior Jarred Whitaker had two touchdowns (one receiving, one defensive) and also added two interceptions. Timmy Thompson had two TDs and Jaiden Cunningham added a touchdown run.
Berea's seven victories this season are the most for the program since 2008.
The Pirates are set to make their first postseason appearance since 2014.
The undefeated Bearcats have been dominant all season.
They have scored 427 points, the most of any Class A team in the state. KCD out-scored its district opponents 159-49.
Senior Dorian Heard has rushed for 1,253 yards and 21 touchdowns on the season. He also has four receiving TDs.
Sophomore quarterback Luke Russo has almost a 1,000 yards passing with 13 touchdowns and senior Nick Smith has 16 total TDs (12 rushing, four receiving).