A total of 76 clubs took part in the first Open Cup tournament in 1914, a majority of whom came from the Northeast region of the country.

In 2008, the Seattle Sounders became the first club in the Professional Era to advance to the semifinals in consecutive seasons after beginning play in the first round.

Since 1996, only five teams have advanced to the semifinals after beginning play in the first round. The Charleston Battery (2008), Carolina RailHawks (2007), San Francisco Bay Seals (1997) and the Seattle Sounders who did it twice in 2007 and 2008. San Francisco remain as the only "third division" club (now the USL Second Division) to advance to the final four during that span.

Since 1995, a USASA team has failed to advance past the first round only three times (1995, 1998, 2002). Uruguay SC from Florida made the second round in back-to-back years (2000, 2001), and Mexico S.C. (Fresno, CA) joined them in 2000. Dallas Roma F.C. advanced in consecutive seasons in 2005 and 2006 and Bavarian S.C. (Milwaukee, WI) advanced in 2003 and 2007. Hollywood United was the lone USASA team to survive the first round in 2008.

In 2006, a record was set when four USASA clubs (Dallas Roma F.C., Sonoma County Sol, Arizona Sahuaros and Milford International) advanced to the second round. The previous record was set the year before when three teams advanced (Dallas Roma F.C., Salinas Valley Samba, Reggae Boyz F.C.).

In 1999, the Wilmington Hammerheads saw two players score hat tricks in their first round match. Ryan Walker and Luke Griffith both scored three times in Wilmington’s 8-1 rout of Los Lobos, a USASA team from Oklahoma.

The Atlanta Silverbacks embarrassed Azzurri, a USASA club from North Texas, 10-0 in the first round of the 2007 tournament. It was the biggest route in the Professional Era, topping the Chicago Stingers’ (USL D3 Pro) 8-0 win over SAC Wisla (USASA) in 1997.