7. 1997 Open Cup: San Francisco Bay Seals 2-1 Kansas City Wizards
Just one year after the first-ever MLS season, teams outside of the division quickly became determined to upset the odds and prove to the country that there was more to soccer outside of the brand new Major League Soccer. So, step forward the San Francisco Bay Seals.
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What made this such a beautiful victory was not just it being the first upset in the MLS Era, but also because it came when the Kansas City Wizards (now Sporting Kansas City) were so dominant in the Western Conference that year, winning the division.
Ultimately, a year prior, MLS distanced itself with all its superiority away from teams such as the Seals, only for the division’s best team — the Wizards — to succumb to defeat from such a team like the Seals. Lovely stuff.
An honorable mention must be said for the Chicago Stingers who beat Colorado Rapids six days later. This was another D3 upset over an MLS side.
Both the Seals and the Stingers made history that year and were the two sides that started the two decades of upsets over MLS sides.