The way Uter gets left behind is mostly like what happened at the end of the 1965 World War II film Von Ryan's Express.
The "Diz-Nee Historical Park" (the new ownership of the Fort Springfield Civil War site) is a reference to Disney's failed attempt to build a historical theme park to be known as Disney's America. The park was to be located close to Manassas Battlefield, and was withdrawn in 1994 due to opposition.
Milhouse's tutor is parody of Tony Randall. (from DVD commentary)
The scene in the bank is a reference the movie It’s a Wonderful Life.
During the teachers's strike, one of the substitute teachers whom Bart drives out is Gabe Kaplan, who played high school teacher and title character Gabe Kotter on Welcome Back, Kotter.
While with a tutor, the blackboard in Milhouse's home reads Colonial Period (1776–1836) when in reality it ended a year before in 1775 after the beginning in 1607. Also if while Milhouse is sitting down, the right side of Milhouse's pants of the behind is colored yellow instead of red, making Milhouse look like he's naked.
In the scene where Bart gets beaten up by the bullies, Dolph is speaking with Jimbo's voice while Kearney is speaking with Dolph's.
While Skinner's speech to the students in the school canteen, two Allison Taylors are seen sitting on different sides of the canteen.
It is a war crime to attack the enemy if they have surrendered. That's the joke.