The first Freeport-Baldwin game took place in 1922. “In those days all you needed was 11 guys, things weren’t that specific,” explained Coach Carroll. Freeport won that year and the next. In 1924, Baldwin beat Freeport, but the Red Devils then went on a winning streak that lasted until 1931. That year “the [Baldwin] Board of Education hired Coach George Craig,” said Coach Carroll. “He was told if you beat Freeport, you have a coaching job for life. And he did. He was Baldwin’s coach for 30 years.” Baldwin had an eight-year winning streak and was known in those early years for its aerial tactics that made Blue and Gold teams famous.

But Freeport hired its own superstar — Coach Bill Ashley — and in 1942 Freeport beat Baldwin 6-0. Newspapers reported that the game drew 12,000 spectators to Freeport Stadium. Back then the game between the two teams took place on Election Day.

In 1950, Freeport and Baldwin were deadlocked at 13 wins each when they faced off. Freeport won 47-13, but Baldwin got revenge the next year in a 12-6 victory. The day before the 1951 face-off, The Leader newspaper reported that at Freeport’s pep rally principal Martin Mansperger presented the team with a sealed envelope which they were to open if they won and burn if they lost. After the game, a Freeport loss, Red Devils’ co-captain Hank Bandhold burned the envelope. No one knows what was inside.

In 1955 the Red Devils won and each “letterman received a white sweater with emblem as a reminder of the season,” wrote The Leader.

By the early 1960s high school football scheduling changed. “We started playing Freeport at the Hofstra Stadium. There were more and more schools playing in the conference,” said Coach Carroll. “There are some years when we don’t play at all; it all depends on where each team falls in preseason rankings.”

Still the competition to be the best on the field remained.

“Those years we had some thrilling games. I think it was sometime around ‘67 or ‘68, we won. It was a big deal. I remember how everybody was driving all over the place. Everybody was so happy. I was a kid but it was cool,” said Carroll, adding, “My brother played the ‘72 game. We were 2-0 with three minutes in the game. Freeport broke a pass on a touchdown and won 6 -2. It was unbelievable!”