Stage 1 United States U23 & Costa Rica U23 (Stage 2)
Caribbean Zone
Stage 1 Jamaica U23 (Stage 2)
- 1 Guyana U23, Suriname U23
- 2 Netherlands Antilles U23, Aruba U23
- 3 Haiti U23, Dominican Republic U23
- 4 Cuba U23, Bahamas U23
- 5 Trinidad & Tobago U23, Saint Vincent & Grenadines U23
- 6 Barbados U23, Saint Lucia U23
- 7 Saint Kitts & Nevis U23, Dominica U23
| Guyana U23 8-4 (Stage 2) | ||||
| Guyana U23, Suriname U23 | ||||
| 15 August 1999 | Georgetown (Guyana) | Guyana U23 | (0) 4-1 (1) | Suriname U23 |
| Guyana U23, Suriname U23 | ||||
| 29 August 1999 | Paramaribo (Suriname) | Suriname U23 | (1) 3-4 (1) | Guyana U23 |
| Netherlands Antilles U23 13-1 (Stage 2) | ||||
| Netherlands Antilles U23, Aruba U23 | ||||
| 25 July 1999 | Oranjestad (Aruba) | Aruba U23 | (0) 0-6 (3) | Netherlands Antilles U23 |
| Netherlands Antilles U23, Aruba U23 | ||||
| 15 August 11999 | Willemstad (Netherlands Antilles) | Netherlands Antilles U23 | (2) 7-1 (0) | Aruba U23 |
| Dominican Republic U23 3-3 (Stage 2) | ||||
| Haiti U23, Dominican Republic U23 | ||||
| 22 August 1999 | Port au Prince (Haiti) | Haiti U23 | (1) 3-2 (0) | Dominican Republic U23 |
| Haiti U23, Dominican Republic U23 | ||||
| 5 September 1999 | San Cristobal (Dominican Republic) | Dominican Republic U23 | (0) 1-0 (0) | Haiti U23 |
| Cuba U23 (Stage 2) |
| Trinidad & Tobago U23 9-1 (Stage 2) | ||||
| Trinidad & Tobago U23, Saint Vincent & Grenadines U23 | ||||
| 27 January 1999 | Kingstown (Saint Vincent & Grenadines) | Saint Vincent & Grenadines U23 | (0) 1-5 (2) | Trinidad & Tobago U23 |
| Trinidad & Tobago U23, Saint Vincent & Grenadines U23 | ||||
| 28 February 1999 | Arima (Trinidad & Tobago) | Trinidad & Tobago U23 | (1) 4-0 (0) | Saint Vincent & Grenadines U23 |
| Barbados U23 5-3 (Stage 2) | ||||
| Barbados U23, Saint Lucia U23 | ||||
| 21 March 1999 | Castries (Saint Lucia) | Saint Lucia U23 | (1) 2-1 (0) | Barbados U23 |
| Barbados U23, Saint Lucia U23 | ||||
| 13 April 1999 | Bridgetown (Barbados) | Barbados U23 | (2) 4-1 (0) | Saint Lucia U23 |
| Saint Kitts & Nevis U23 3-1 (Stage 2) | ||||
| Saint Kitts & Nevis U23, Dominica U23 | ||||
| 4 July 1999 | Roseau (Dominica) | Dominica U23 | (1) 1-1 (1) | Saint Kitts & Nevis U23 |
| Saint Kitts & Nevis U23, Dominica U23 | ||||
| 18 July 1999 | Basseterre (Saint Kitts & Nevis) | Saint Kitts & Nevis U23 | (0) 2-0 (0) | Dominica U23 |
Stage 2
- 1 Guyana U23, Netherlands Antilles U23
- 2 Netherlands Antilles U23, Aruba U23
- 3 Haiti U23, Dominican Republic U23
- 4 Cuba U23, Bahamas U23
| Netherlands Antilles U23 1-1 (Stage 2) | ||||
| Guyana U23, Netherlands Antilles U23 | ||||
| 19 September 1999 | Georgetown (Guyana) | Guyana U23 | (1) 1-1 (0) | Netherlands Antilles U23 |
| Guyana U23, Netherlands Antilles U23 | ||||
| 26 September 1999 | Willemstad (Netherlands Antilles) | Netherlands Antilles U23 | (0) 0-0 (0) | Guyana U23 |
| Cuba U23 7-0 (Inter Zone) | ||||
| Cuba U23, Dominican Republic U23 | ||||
| 19 September 1999 | Santo Domingo (Dominican Republic) | Dominican Republic U23 | (0) 0-4 (2) | Cuba U23 |
| Cuba U23, Dominican Republic U23 | ||||
| 24 September 1999 | Havana (Cuba) | Cuba U23 | (1) 3-0 (0) | Dominican Republic U23 |
| Trinidad & Tobago U23 6-3 (Inter Zone) | ||||
| Trinidad & Tobago U23, Barbados U23 | ||||
| 3 October 1999 | Port of Spain (Trinidad & Tobago) | Trinidad & Tobago U23 | (3) 4-1 (1) | Barbados U23 |
| Trinidad & Tobago U23, Barbados U23 | ||||
| 17 October 1999 | Bridgetown (Barbados) | Barbados U23 | (2) 2-2 (0) | Trinidad & Tobago U23 |
| Jamaica U23 5-2 (Stage 2) | ||||
| Jamaica U23, Saint Kitts & Nevis U23 | ||||
| 19 September 1999 | Basseterre (Saint Kitts & Nevis) | Saint Kitts & Nevis U23 | (0) 1-3 (2) | Jamaica U23 |
| Jamaica U23, Saint Kitts & Nevis U23 | ||||
| 26 September 1999 | Kingston (Jamaica) | Jamaica U23 | (0) 2-1 (1) | Saint Kitts & Nevis U23 |
Central American Zone
Stage 1
| Guatemala U23 9-2 (Stage 2) | ||||
| Guatemala U23, Belize U23 | ||||
| 12 September 1999 | San Ignacio (Belize) | Belize U23 | (0) 1-3 (1) | Guatemala U23 |
| Guatemala U23, Belize U23 | ||||
| 19 September 1999 | Guatemala City (Guatemala) | Guatemala U23 | (3) 6-1 (1) | Belize U23 |
| Panama U23 3-2 (Stage) | ||||
| El Salvador U23, Panama U23 | ||||
| 5 September 1999 | San Salvador (Belize) | El Salvador U23 | (0) 1-2 (1) | Panama U23 |
| El Salvador U23, Panama U23 | ||||
| 12 September 1999 | Panama City (Panama) | Panama U23 | (0) 1-1 (0) | El Salvador U23 |
| Honduras U23 10-2 (Stage 2) | ||||
| Honduras U23, Nicaragua U23 | ||||
| 5 September 1999 | Diriamba (Nicaragua) | Nicaragua U23 | (0) 0-6 (4) | Honduras U23 |
| Honduras U23, Nicaragua U23 | ||||
| 12 September 1999 | San Pedro Sula (Honduras) | Honduras U23 | (1) 4-2 (0) | Nicaragua U23 |
Stage 2 United States U23 (Host) (Olympic Games Australia 2000 North & Central American Caribbean Zone Qualifying)
- Group A Trinidad & Tobago U23 (Host), Guatemala U23, Canada U23, Netherlands Antilles U23
- Group B Mexico U23 (Host), Jamaica U23, Honduras U23, Costa Rica U23
- Group C Cuba U23, Panama U23 (Host), Bermuda U23
Group C United States U23, Cuba U23, Panama U23 (Host), Bermuda U23
| Guatemala U23, Canada U23 | ||||
| 21 March 2000 | Port of Spain (Trinidad & Tobago) | Guatemala U23 | (0) 0-0 (0) | Canada U23 |
| Trinidad & Tobago U23, Netherlands Antilles U23 | ||||
| 21 March 2000 | Port of Spain (Trinidad & Tobago) | Trinidad & Tobago U23 | (1) 6-0 (0) | Netherlands Antilles U23 |
| Canada U23, Netherlands Antilles U23 | ||||
| 23 March 2000 | Port of Spain (Trinidad & Tobago) | Canada U23 | (0) 1-0 (0) | Netherlands Antilles U23 |
| Trinidad & Tobago U23, Guatemala U23 | ||||
| 23 March 2000 | Port of Spain (Trinidad & Tobago) | Trinidad & Tobago U23 | (0) 0-0 (0) | Guatemala U23 |
| Guatemala U23, Netherlands Antilles U23 | ||||
| 25 March 2000 | Port of Spain (Trinidad & Tobago) | Guatemala U23 | (5) 9-1 (0) | Netherlands Antilles U23 |
| Trinidad & Tobago U23, Canada U23 | ||||
| 25 March 2000 | Port of Spain (Trinidad & Tobago) | Trinidad & Tobago U23 | (0) 0-2 (1) | Canada U23 |
| 1 | Canada U23 | 3 | 2 | 1 | 0 | 3-0 | 3 | 7 |
| 2 | Guatemala U23 | 3 | 1 | 2 | 0 | 9-1 | 8 | 5 |
| 3 | Trinidad & Tobago U23 | 3 | 1 | 1 | 1 | 6-2 | 4 | 4 |
| 4 | Netherlands Antilles U23 | 3 | 0 | 0 | 3 | 1-16 | -15 | 0 |
| Jamaica U23, Costa Rica U23 | ||||
| 4 April 2000 | Guadalajara (Mexico) | Jamaica U23 | (1) 1-2 (2) | Costa Rica U23 |
| Mexico U23, Honduras U23 | ||||
| 4 April 2000 | Guadalajara (Mexico) | Mexico U23 | (0) 2-2 (2) | Honduras U23 |
| Honduras U23, Costa Rica U23 | ||||
| 6 April 2000 | Guadalajara (Mexico) | Costa Rica U23 | (1) 1-1 (1) | Honduras U23 |
| Mexico U23, Jamaica U23 | ||||
| 6 April 2000 | Guadalajara (Mexico) | Mexico U23 | (2) 5-0 (0) | Jamaica U23 |
| Jamaica U23, Honduras U23 | ||||
| 8 April 2000 | Guadalajara (Mexico) | Jamaica U23 | (0) 0-2 (1) | Honduras U23 |
| Mexico U23, Costa Rica U23 | ||||
| 8 April 2000 | Guadalajara (Mexico) | Mexico U23 | (2) 5-1 (0) | Costa Rica U23 |
| 1 | Mexico U23 | 3 | 2 | 1 | 0 | 12-3 | 9 | 7 |
| 2 | Honduras U23 | 3 | 1 | 2 | 0 | 5-3 | 2 | 5 |
| 3 | Costa Rica U23 | 3 | 1 | 1 | 1 | 4-7 | -3 | 4 |
| 4 | Jamaica U23 | 3 | 0 | 0 | 3 | 1-9 | -8 | 0 |
| Panama U23, Bermuda U23 | ||||
| 5 April 2000 | Panama City (Panama)</ | Panama U23 | (1) 1-0 (0) | Bermuda U23 |
| Cuba U23, Bermuda U23 | ||||
| 7 April 2000 | Panama City (Panama) | Cuba U23 | (0) 0-0 (0) | Bermuda U23 |
| Cuba U23, Panama U23 | ||||
| 9 April 2000 | Panama City (Panama) | Panama U23 | (0) 1-1 (0) | Cuba U23 |
| 1 | Panama U23 | 2 | 1 | 1 | 0 | 2-1 | 1 | 4 |
| 2 | Cuba U23 | 2 | 0 | 2 | 0 | 1-1 | 0 | 2 |
| 3 | Bermuda U23 | 2 | 0 | 1 | 1 | 1-2 | -1 | 1 |