Jeff references Family Day, which doesn't happen until "Basic Genealogy," because they were aired out of order from production.
When Coach Bogner and Jeff play pool, Jeff breaks and pockets a two-colored ball (15). After that Jeff continues and plays one-colored balls. Soon after that Coach Bogner is seen pocketing ball number 15.
The positions of the balls change drastically in between the shots. It is especially obvious when coach Bogner is about to take his last shot.
Troy referencing that Can't Buy Me Love is a remake of a movie made 16 years later is a joke about how TV shows and movies are remade for different markets based on race in the US. In the same way the joke about After School Specials and Fat Albert exists (they both started a month of each other in 1972).
Troy references Calvin (from Calvin and Hobbes) saying "...if anything got in his way, he just peed on it." However, this was never an aspect of the comic strip. It is something that has often been depicted in recreations, graffiti, vehicle stencil detailing, etc. but was not part of any Calvin and Hobbes original content.