Here is the schedule for the 1998 U.S. Open Cup: FIRST ROUND Eight matches to be played between June 9 and June 21
| Date | Matchup/Result |
| June 9 | Austin (D3 Pro) 2 San Nicholas (USASA Region IV) 1 |
| June 10 | Delaware (D3 Pro) 2 Detroit (Premier) 1 (OT) |
| June 11 | Wisla (USASA Region II) at Chicago (D3 Pro) |
| June 12 | Los Lobos (USASA Region III) at Charlotte (D3 Pro) |
| June 12 | San Gabriel Valley (Premier) at Arizona (D3 Pro) |
| June 13 | Kansas City (Premier) at Central Jersey (D3 Pro) |
| June 16 | Jackson (Premier) at Orlando (D3 Pro) |
| June 21 | USASA Region I at Western Mass. (D3 Pro) |
- Jackson/Orlando winner vs. Milwaukee (Game 1)
- Kansas City/Central Jersey winner vs. Hampton Roads (Game 2)
- Los Lobos/Charlotte winner vs. Worcester (Game 3)
- Region I champ/Western Mass. winner vs. Rochester (Game 4)
- Wisla/Chicago winner vs. Hershey (Game 5)
- San Gabriel Valley/Arizona winner vs. El Paso (Game 6)
- Delaware (D3 Pro) vs. Nashville (Game 7)
- Austin (D3 Pro) vs. Orange County (Game 8)
- Game 1 winner vs. Miami
- Game 2 winner vs. MetroStars
- Game 3 winner vs. Tampa Bay
- Game 4 winner vs. Columbus
- Game 5 winner vs. Chicago
- Game 6 winner vs. San Jose
- Game 7 winner vs. Kansas City
- Game 8 winner vs. Dallas
