| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 8/17/25 | Olimpia vs Libertad | Primera Division - Clausura | 0:0 | No | No |
| 5/22/25 | Olimpia vs Libertad | Primera Division - Clausura | 1:1 | No | Yes |
| 3/16/25 | Libertad vs Olimpia | Primera Division - Clausura | 2:1 | Yes | Yes |
| 1/23/25 | Libertad vs Olimpia | Professional League | 2:1 | Yes | Yes |
| 10/21/24 | Libertad vs Olimpia | Primera Division - Clausura | 0:1 | No | No |
| 8/11/24 | Olimpia vs Libertad | Primera Division - Clausura | 4:0 | Yes | No |
| 6/6/24 | Olimpia vs Libertad | Primera Division - Clausura | 1:3 | Yes | Yes |
| 3/31/24 | Libertad vs Olimpia | Primera Division - Clausura | 0:0 | No | No |
| 11/26/23 | Olimpia vs Libertad | Primera Division - Clausura | 1:3 | Yes | Yes |
| 9/28/23 | Libertad vs Olimpia | Primera Division - Clausura | 4:0 | Yes | No |
| 5/21/23 | Libertad vs Olimpia | Primera Division - Clausura | 1:0 | No | No |
| 3/19/23 | Olimpia vs Libertad | Primera Division - Clausura | 2:1 | Yes | Yes |
| 10/13/22 | Olimpia vs Libertad | Primera Division - Clausura | 1:0 | No | No |
| 9/8/22 | Olimpia vs Libertad | Division Intermedia | 0:4 | Yes | No |
| 7/20/22 | Libertad vs Olimpia | Primera Division - Clausura | 4:2 | Yes | Yes |
| 5/8/22 | Libertad vs Olimpia | Primera Division - Clausura | 1:0 | No | No |
| 2/21/22 | Olimpia vs Libertad | Primera Division - Clausura | 2:2 | Yes | Yes |
| 11/27/21 | Olimpia vs Libertad | Primera Division - Clausura | 2:3 | Yes | Yes |
| 11/14/21 | Olimpia vs Libertad | Division Intermedia | 2:1 | Yes | Yes |
| 9/13/21 | Libertad vs Olimpia | Primera Division - Clausura | 0:3 | Yes | No |
| 4/4/21 | Libertad vs Olimpia | Primera Division - Clausura | 0:1 | No | No |
| 2/8/21 | Olimpia vs Libertad | Primera Division - Clausura | 0:1 | No | No |
| 12/20/20 | Libertad vs Olimpia | Primera Division - Clausura | 2:1 | Yes | Yes |
| 8/14/20 | Olimpia vs Libertad | Primera Division - Clausura | 2:1 | Yes | Yes |
| 1/26/20 | Libertad vs Olimpia | Primera Division - Clausura | 1:1 | No | Yes |
| 10/27/19 | Olimpia vs Libertad | Primera Division - Clausura | 2:1 | Yes | Yes |
| 8/6/19 | Libertad vs Olimpia | Primera Division - Clausura | 2:0 | No | No |
| 4/28/19 | Olimpia vs Libertad | Primera Division - Clausura | 3:0 | Yes | No |
| 2/24/19 | Libertad vs Olimpia | Primera Division - Clausura | 2:3 | Yes | Yes |
| 11/25/18 | Libertad vs Olimpia | Primera Division - Clausura | 0:2 | No | No |
| 9/9/18 | Olimpia vs Libertad | Primera Division - Clausura | 1:0 | No | No |
| 12/2/17 | Olimpia vs Libertad | Primera Division - Clausura | 1:0 | No | No |
| 9/24/17 | Libertad vs Olimpia | Primera Division - Clausura | 2:1 | Yes | Yes |
| 6/10/17 | Libertad vs Olimpia | Primera Division - Clausura | 3:0 | Yes | No |
| 3/30/17 | Olimpia vs Libertad | Primera Division - Clausura | 0:3 | Yes | No |
| 12/4/16 | Libertad vs Olimpia | Primera Division - Clausura | 2:2 | Yes | Yes |
| 8/28/16 | Olimpia vs Libertad | Primera Division - Clausura | 1:1 | No | Yes |
| 4/28/16 | Libertad vs Olimpia | Primera Division - Clausura | 3:1 | Yes | Yes |
| 1/31/16 | Olimpia vs Libertad | Primera Division - Clausura | 1:0 | No | No |
| 9/28/15 | Libertad vs Olimpia | Primera Division - Clausura | 1:1 | No | Yes |
| 7/10/15 | Olimpia vs Libertad | Primera Division - Clausura | 1:1 | No | Yes |
| 5/9/15 | Libertad vs Olimpia | Primera Division - Clausura | 2:2 | Yes | Yes |
| 3/7/15 | Olimpia vs Libertad | Primera Division - Clausura | 1:2 | Yes | Yes |
| 11/13/14 | Olimpia vs Libertad | Primera Division - Clausura | 0:1 | No | No |
| 9/7/14 | Libertad vs Olimpia | Primera Division - Clausura | 3:1 | Yes | Yes |
| 6/28/14 | Libertad vs Olimpia | Primera Division - Clausura | 1:0 | No | No |
| 4/28/14 | Olimpia vs Libertad | Primera Division - Clausura | 2:1 | Yes | Yes |
| 10/19/13 | Olimpia vs Libertad | Primera Division - Clausura | 1:2 | Yes | Yes |
| 8/6/13 | Libertad vs Olimpia | Primera Division - Clausura | 1:0 | No | No |
| 6/21/13 | Olimpia vs Libertad | Primera Division - Clausura | 2:1 | Yes | Yes |
| 4/15/13 | Libertad vs Olimpia | Primera Division - Clausura | 0:0 | No | No |
| 11/4/12 | Libertad vs Olimpia | Primera Division - Clausura | 1:1 | No | Yes |
| 8/20/12 | Olimpia vs Libertad | Primera Division - Clausura | 2:2 | Yes | Yes |
| 6/13/12 | Olimpia vs Libertad | Primera Division - Clausura | 2:1 | Yes | Yes |
| 3/10/12 | Libertad vs Olimpia | Primera Division - Clausura | 0:1 | No | No |
| 10/30/11 | Olimpia vs Libertad | Primera Division - Clausura | 0:2 | No | No |
| 8/16/11 | Libertad vs Olimpia | Primera Division - Clausura | 2:1 | Yes | Yes |