West Nottingham Academy found itself playing on back-to-back days in 1945 due to an administrative oversight — but all worked out well as the Rams won both outings.
The story goes like this, WNA’s 1944 coach Charles Remaley scheduled Baltimore Friends for Oct. 19, 1945. Remaley left WNA after the 1944-45 school year and Paul R. Davis inherited the varsity program. Not realizing Remaley had scheduled an Oct. 19 contest, Davis locked down an Oct. 20 date with Massanutten Military Academy (Va.). There was little option when West Nottingham Academy found out about the error — and WNA decided to honor both contracts, playing games on consecutive days.
WNA defeated Baltimore Friends 24-6 and the next afternoon edged Massanutten 13-6 on its way to a 6-2 season.
Maryland High School Football Reference 