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 | Chicago (D3 Pro) 8 Wisla (USASA Region II) 0 |
| June 12 | Charlotte (D3 Pro) 4 Los Lobos (USASA Region III) 3 |
| June 12 | Arizona (D3 Pro) 2 San Gabriel Valley (Premier) 1 |
| June 13 | Central Jersey (D3 Pro) 2 Kansas City (Premier) 1 (OT) |
| June 16 | Orlando (D3 Pro) 2 Jackson (PDSL) 1 |
| June 21 | (N.Y.) Greek Americans at Western Mass. (D3 Pro) |
- Orlando (D3 Pro) vs. Milwaukee Rampage (Game 1)
- Central Jersey (D3 Pro) vs. Hampton Roads Mariners (Game 2)
- Charlotte (D3 Pro) vs. Worcester Wildfire (Game 3)
- Greek Americans/Western Mass. winner vs. Rochester Rhinos (Game 4)
- Chicago (D3 Pro) vs. Hershey Wildcats (Game 5)
- Arizona (D3 Pro) vs. El Paso Patriots (Game 6)
- Delaware (D3 Pro) vs. Nashville Metros (Game 7)
- Austin (D3 Pro) vs. Orange County Zodiac (Game 8)
- Game 1 winner vs. Miami Fusion
- Game 2 winner vs. MetroStars
- Game 3 winner vs. Tampa Bay Mutiny
- Game 4 winner vs. Columbus Crew
- Game 5 winner vs. Chicago Fire
- Game 6 winner vs. San Jose Clash
- Game 7 winner vs. Kansas City Wizards
- Game 8 winner vs. Dallas Burn
