Most of the records listed below are courtesy of Coach John Nania and are subject to change as records are broken and/or with further research or as new records are brought to the current coaching staff's attention. If possible please include documentation to back any and all potential records.

Undefeated Seasons: 1917 & 1961
Highest State Ranking to end season: 19th - 1994
 

Scoring
 

Most TDs (season): 36: 1912, 1922, and 1965
Most Points Scored (season): 243: 1965 (8 games)
Most Points Scored (game): 103 vs. Highland Falls 1922
Most Points Scored (half): 54: 10/28/22
Most Points Scored (quarter): 40: 10/28/22
Lowest Score in a Middletown victory: 2-0 vs. Kingston, 1935
Most Points Overcome to Victory: 15: vs M-W: 10/7/94
 

Offense
 

Most Yards rushing (game): 528 yards: 11/8/30
Most Yards rushing (season): 1,925 yards: 1970
Most 1st Downs (game): 23: 10/3/64
Most 1st Downs (season): 97: 1966
 

Defense
 

Most INTs (game): 7 vs. Ithaca HS, 10/25/41
Most Fumbles Recovered (game): 6: vs PJ 11/26/53 & vs Mt. Pleasant 9/22/45
Most Punt Blocks (season): 5: 1946