1986–1989 Football
Season-level index for the final years before the modern Section IX playoff structure fully took shape.
1986
OCL champion: Port Jervis, which beat Pine Bush 20–14 in the title game. MHAL champion: Rondout Valley. WSL champion: Jeffersonville-Youngsville.
1987
Kingston and Newburgh returned to Section IX. Port Jervis beat Kingston 6–2 for the OCL title. Rondout Valley won the MHAL; Jeffersonville-Youngsville won the WSL.
1988
Monroe-Woodbury beat Port Jervis 34–0 for the OCL title. Red Hook and Onteora shared the MHAL title. Liberty won the WSL.
1989
Sectional champions: Monroe-Woodbury (A), Onteora (B), Red Hook (C), Roscoe (D). Those four advanced to the state-quarterfinal round, marking the beginning of the sectional postseason record now indexed separately by KOT845.