1. Open Cup 2006: Dallas Roma FC 0-0 Chivas USA (Dallas advances 4-2 in PKs)
This victory is so astonishing, it just captures all the reasons why we love cup soccer.
Every year the U.S Open Cup comes around, the unthinkable victory from USASA side Dallas Roma FC over MLS side Chivas USA rings through the memory files.
It remains, to this day, the most shocking upset for many reasons. The fact that Dallas not only defeated an MLS giant, but also legendary coach Bob Bradley as well, the fact the club had to pay thousands of dollars they didn’t have just to get the ball rolling in the first place. Each minor and every major detail poetically summarized why the U.S Open Cup is so special and why this game was as much of an upset as you will see.
Dallas Roma’s victory over the Chivas USA was the first-ever time a team from the USASA has upset an MLS side, and, as a result, it remains the most memorable MLS upset in U.S Open Cup history.