The 85th Annual Pep Rally was an infamous Middleton High School Pep Rally which saw the first Pom-Pom victory in Middleton's history.
The Middleton Pep Rally is the oldest pep rally in American history. Despite having spanned multiple decades, the Middleton Pep Rally has always adhered to a nearly identical format: an address from the Principal and Student President followed by an appearance from the school mascot followed by the ceremonial "melon smash" followed by a dance-off between the Pom Pom's and the Cheerleaders. Up until the 85th year, the Cheerleader's had stood as uncontested victors, leading one journalist to remark that "watching the Pom's lose has become a tradition as sepia-hued and cozily familiar as Christmas morning".
Due to the Cheerleader's uncontested winning streak, the Pom's loss of their new uniforms, and the general shoddiness of Penelope's squad, expectations were low for a Pom victory. Only school mascot Ronnie the Rabbit expressed faith in the Pom's, which many believed was the result of brain damage due to his heavy drug use.
During the dance-off, the Cheerleaders initially looked favorable to win due to a flawless routine that contrasted heavily with the Pom's under-rehearsed and "sweaty" moves. However, critical favor was promptly swayed towards the Poms when second-tier cheerleader Robertha accidentally dropped Cynthia, resulting in a brutal career-ending leg injury. Judges unanimously declared a Pom-Pom victory, making Penelope and her squad the first Pom's in history to win the Middleton Pep Rally Dance-Off.
In the wake of the 85th Annual Pep Rally, speculation has persisted as to the validity of the Pom victory. Many claim that Robertha's fatal mistake was unnaturally spontaneous, and was likely the result of foul play. Certain conspiracists claim to have seen a laser pointer projected into Robertha's eye during the critical moment of error, although these reports have not been officially substantiated. Penelope's victory currently stands uncontested.