1999 Copa Bolivia
 |
| Tournament details | |
|---|---|
| Country | Bolivia  |
| Defending champions | Club Jorge Wilstermann |
| Final positions | |
| Champions | Oriente Petrolero (9th title) |
| Runner-up | Bolivar |
This is the fourth edition of the Copa Bolivia, Jorge Wilstermann are the defending after beating 2-1 (On Aggregate) Blooming. The format of the Copa Bolivia had change it is going to be only knockout in the 1st round team from third division qualified. The second round is for 2nd division, 3rd round for the 1st Division.
First round
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Club Litoral | 4–2 | Always Ready | 2–2 | 2–0 |
| 31 de Octubre | 0–1 | Municipal de Tarija | 0–0 | 0–1 |
| Bolivar Nimbles | 1–4 | Real Cochabamba | 1–3 | 0–1 |
| Club Real Camba | 0–2 | Universitario de Potosi | 0–2 | 0–0 |
| Club Callejas | 3–2 | 12 De October | 2–2 | 1–0 |
| Club America | 1–3 | Pando F.C | 1–2 | 0–1 |
Second round
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Club Litoral | 1–0 | ABB | 0–0 | 1–0 |
| Universitario de Potosi | 2–3 | Municipal de Tarija | 2–0 | 0–3 |
| Deportivo Cristal | 2–0 | Universidad de Santa Cruz | 1–0 | 1–0 |
| Real Cochabamba | (a)3–3 | Chaco Petrolero | 1–0 | 2–3 |
| Universitario de Potosi | 2–4 | Fraternidad Tigres | 0–2 | 2–2 |
| Enrique Happ | 2–2(a) | Club Stormers San Lorenzo | 2–1 | 0–1 |
| Universitario de Pando | 0–1 | Mariscal Santa Cruz | 0–0 | 0–1 |
| Club Callejas | 3–2 | Pando F.C | 2–1 | 1–1 |
Third round
- 4 best loser from the 2nd round.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Club Litoral | 1–0 | Blooming | 0–0 | 1–0 |
| Municipal de Tarija | 0–5 | Bolívar | 0–1 | 0–4 |
| Real Cochabamba | 3–4 | Real Potosí | 2–1 | 1–3 |
| Fraternidad Tigres | 0–1 | Club Unión Central | 0–0 | 0–1 |
| Independiente Petrolero | 2–3 | Universitario de Pando | 2–1 | 0–2 |
| Guabirá | (a)4–4 | Real Santa Cruz | 2–0 | 2–4 |
| Jorge Wilstermann | 2–1 | San José | 1–1 | 1–0 |
| Club Destroyers | 3–6 | Oriente Petrolero | 2–3 | 1–3 |
| ABB | 2–4 | The Strongest | 2–1 | 0–3 |
| Universitario de Potosi | 4–5 | Club Callejas | 4–3 | 0–2 |
| Chaco Petrolero | 1–2 | Mariscal Santa Cruz | 1–1 | 0–1 |
| Enrique Happ | 0–4 | Club Stormers San Lorenzo | 0–0 | 0–4 |
Fourth round
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Club Litoral | 4–3 | Club Callejas | 2–3 | 2–1 |
| Bolívar | 6–4 | Mariscal Santa Cruz | 3–3 | 2–1 |
| Real Potosí | 1–3 | Club Stormers San Lorenzo | 1–0 | 0–3 |
| Club Unión Central | 1–5 | Oriente Petrolero | 1–3 | 0–2 |
| Universitario de Pando | 0–2 | Guabirá | 0–0 | 0–2 |
| The Strongest | 2–1 | Jorge Wilstermann | 1–1 | 1–0 |
Quarter-final
- 2 Best Loser
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Club Callejas | 1–4 | Bolívar | 1–2 | 0–2 |
| Club Stormers San Lorenzo | 0–5 | The Strongest | 0–2 | 0–3 |
| Club Litoral | 5–5(a) | Guabirá | 5–3 | 0–2 |
| Jorge Wilstermann | 2–4 | Oriente Petrolero | 2–4 | 0–0 |
Semi-final
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Bolívar | 5–2 | The Strongest | 3–0 | 2–2 |
| Oriente Petrolero | 4–1 | Guabirá | 2–0 | 2–1 |
Final
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Oriente Petrolero | 7–6 | Bolívar | 4–3 | 3–3 |