The Men's Boxing Tournament at the 1999 Pan American Games was held in Winnipeg, Manitoba, Canada from July 31 to August 8. It served as a qualification tournament for the 2000 Summer Olympics in Sydney, Australia. The number one and two earned a ticket for the Olympic Tournament.
| Light Flyweight ( - 48 kilograms) |  Maikro Romero |  Liborio Romero |  Iván Calderón Patricio Calero | |
| Flyweight ( - 51 kilograms) |  Omar Andrés Narváez |  José Navarro | Daniel Ponce de León Manuel Mantilla | |
| Bantamweight ( - 54 kilograms) | Gerald Tucker | Nehomar Cermeno | Waldemar Font Ceferino Labarda | |
| Featherweight ( - 57 kilograms) | Yudel Johnson |  Zayas Younan | Jorge Martínez Aaron Torres | |
| Lightweight ( - 60 kilograms) | Mario Kindelán | Dana Laframboise | Patrick López Cristian Bejarano | |
| Light Welterweight ( - 63.5 kilograms) | Victor Hugo Castro |  Kelson Santos | Diógenes Luña Corey Bernard | |
| Welterweight ( - 67 kilograms) | Juan Hernández Sierra | Jeremy Molitor | LeChaunce Shepherd Charlie Navarro | |
| Light Middleweight ( - 71 kilograms) | Jorge Gutiérrez | Scott MacIntosh | Darnell Wilson David Sean Black | |
| Middleweight ( - 75 kilograms) | Yohanson Martínez | Arthur Palac |  José HerreraJim Rodriguez | |
| Light Heavyweight ( - 81 kilograms) | Humberto Savigne | Laudelino Barros | Troy Amos-Ross Hugo Garay | |
| Heavyweight ( - 91 kilograms) | Odlanier Solis | Mark Simmons | Marcelino Novaes Kerron Speid | |
| Super Heavyweight (+ 91 kilograms) | Alexis Rubalcaba | Davin King | Claudio Silva Manuel Azar |
| width=50 | Place | width=200 | Nation | width=50 | width=50 | width=50 | width=50 | Total | |||
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | 9 | 0 | 3 | 12 | |||||||
| 2 | 2 | 0 | 3 | 5 | |||||||
| 3 | 1 | 3 | 4 | 8 | |||||||
| 4 | 0 | 5 | 1 | 6 | |||||||
| 5 | 0 | 2 | 2 | 4 | |||||||
| 6 | 0 | 1 | 3 | 4 | |||||||
| 0 | 1 | 3 | 4 | ||||||||
| 8 | 0 | 0 | 2 | 2 | |||||||
| 9 | 0 | 0 | 1 | 1 | |||||||
| 0 | 0 | 1 | 1 | ||||||||
| 0 | 0 | 1 | 1 | ||||||||
| Total | 12 | 12 | 24 | 48 |