| 1999 Junior League World Series | |
| Start Date: | August 16 |
| End Date: | 21 |
| Champion: | -->  Arroyo, Puerto Rico |
| Runner-Up1: | -->  Hermosillo, Mexico |
| Runner-Up2: | --> |
| Previous: | 1998 |
| Next: | 2000 |
The 1999 Junior League World Series took place from August 16–21 in Taylor, Michigan, United States. Arroyo, Puerto Rico defeated Hermosillo, Mexico in the championship game.
This year featured the debut of the Far East region.
| United States | International | |
|---|---|---|
| Fort Wayne, Indiana St Joe Central Central |  Coquitlam, British ColumbiaCoquitlam Canada | |
| Meriden, Connecticut Ed Walsh East | Ramstein, Germany KMC Europe | |
| Lake Charles, Louisiana South Lake Charles South |  Hagåtña, GuamFar East | |
| La Verne, California La Verne West | Hermosillo, Sonora Mexico | |
| Arroyo, Puerto Rico Arroyo Puerto Rico |
Winner's Bracket
Loser's Bracket
Elimination Round