Many of the songs from Underdog Alma Mater had already been released in the band's previous EPs.
The band's very first EP, Television Off, Party On, featured the tracks "Believe Me, I'm Lying", "She's a Lady", and "Breakdown". However, these tracks have a significantly different sound to them in their respective recordings from the EP and Underdog Alma Mater. On the band's release, The Sickest Warped Tour EP, "Hey Brittany" and "Coffee Break" were featured on it, but were also different from their respective recorded versions on the album. Unlike the other songs, on the band's EP, Hot Party Jamz, the track "That for Me" was featured, but its recording remained the same as it was on the album.
During the writing of the songs for the album, guitarist Marc Stewart stated, "Our songs are about real stuff that's happened to us because that's what kids want to hear about. They want to listen to stories about things that could happen to them as well, or that already have happened to them."
The track "Believe Me, I'm Lying", written by Austin Bello and Caleb Turman, is based on how Turman once ran into trouble with his girlfriend after he lied to her and left her in tears. Turman stated, "I was hanging out with some other girls, but I told my girlfriend that I was going out by myself. So, the girls and I decided to get some coffee, and as we're walking to the car, my girlfriend pulled up and her headlights were right there in my face. I was totally busted."
"Believe Me, I'm Lying" and the track "My Worst Nightmare" were both written by Bello and Turman and both tracks had originally descended from the duo's former acoustic/electronic project Been Bradley. The original recordings of these two songs are featured on the deluxe edition of Underdog Alma Mater.
On July 7, 2009, the deluxe edition of the album was released. It featured the twelve original songs from the album and seventeen additional tracks from the band, mainly from the band's earlier days. A DVD with live shows and other footage was also included, as well.