1999 Summer League Award Balloting Totals
Most Valuable Player
| Player | Team | Total |
| Griffey | Chicago | 76 (4) |
| Rodriguez, A | Liverpool | 67 (2) |
| McGwire | Hibbing-Gilmer | 56 (2) |
| Bonds | Windy City | 55 |
| Guerrero, V | Andrews | 50 |
| Vaughn, G | Hibbing | 38 |
| Galarraga | Palatine | 31 |
| Gonzalez, J | Liverpool | 26 (1) |
| Belle | Barstow | 19 |
| Thomas, F | Windy City | 19 |
| Olerud | Liverpool | 14 |
| Biggio | Arvada | 11 |
| Jones, "C" | Arvada | 9 |
| Alou | Chicago | 6 |
| Larkin | Barstow | 5 |
| Sosa | Gilmer-Hibbing | 4 |
| Offerman | Barstow | 3 |
| Kendall | Palatine | 2 |
| Rodriguez, I | Chicago | 2 |
| Rolen | Windy City | 1 |
| DiSarcina | Gilmer | 1 |
Cy Young
| Player | Team | Total |
| Maddux | Liverpool | 40 (8) |
| Moyer | Liverpool | 22 |
| Brown | Andrews | 18 |
| Leiter | Barstow | 15 |
| Hoffman | Barstow | 11 |
| Urbina | Liverpool | 11 |
| Smoltz | Andrews | 9 |
| Nen | Andrews | 7 (1) |
| Johnson, R | Arvada | 2 |
Gold Gloves
as determined by a special panel
| P | Bartolo Colon | Andrews-Chicago |
| C | Pudge Rodriguez | Chicago |
| 1B | David Segui | Arvada |
| 2B | Damion Easley | Andrews |
| SS | (tie) Barry Larkin | Barstow |
| SS | (tie) Omar Vizquel | Andrews |
| 3B | Robin Ventura | Liverpool |
| OF | Jim Edmonds | Gilmer |
| OF | Raul Mondesi | Windy City |
| OF | Larry Walker | Liverpool |
Silver Sluggers
as determined by a special panel
| C | (tie) Jason Kendall | Palatine |
| C | (tie) Mike Piazza | Barstow |
| 1B | Mark McGwire | Hibbing-Gilmer |
| 2B | Craig Biggio | Arvada |
| SS | Alex Rodriguez | Liverpool |
| 3B | Chipper Jones | Arvada |
| OF | Ken Griffey | Chicago |
| OF | Vladimir Guerrero | Andrews |
| OF | Barry Bonds | Windy City |
| DH | Greg Vaughn | Hibbing |