Finding Wikipedia's Saddest College Football Rivalry Pages
Boston College vs. UMass The Minutemen have won twice since 1912. Sure, they've only played 24 times in total, but 1912 was more than a century ago, in my opinion.
http://www.sbnation.com/college-football/2014/8/16/6021427/finding-wikipedias-saddest-college-football-rivalry-pages