Copa Libertadores 2023, Round of 16 |
| 10.08.2023 | | Olimpia | | Flamengo | | 3:1 (1:1) |
| Asunción |
Copa Libertadores 2023, Group H |
| 27.06.2023 | | Olimpia | | Melgar | | 4:1 (4:0) |
| Asunción |
Copa Libertadores 2023, Group H |
| 08.06.2023 | | Olimpia | | Atlético Nacional | | 3:0 (1:0) |
| Asunción |
Copa Libertadores 2023, Group H |
| 25.05.2023 | | Patronato | | Olimpia | | 0:2 (0:1) |
| Santa Fe |
Copa Libertadores 2023, Group H |
| 18.04.2023 | | Olimpia | | Patronato | | 1:0 (1:0) |
| Asunción |
Copa Libertadores 2022, Group G |
| 25.05.2022 | | Cerro Porteño | | Olimpia | | 0:1 (0:1) |
| Asunción |
Copa Libertadores 2022, Group G |
| 04.05.2022 | | Olimpia | | Peñarol | | 1:0 (1:0) |
| Asunción |
Copa Libertadores 2022, Third round |
| 16.03.2022 | | Olimpia | | Fluminense | | 2:0 (1:0), pen. 4:1 |
| Asunción |
Copa Libertadores 2022, Second round |
| 24.02.2022 | | Olimpia | | Atlético Nacional | | 3:1 (1:0) |
| Asunción |
Copa Libertadores 2022, First Round |
| 16.02.2022 | | Olimpia | | Universidad César Vallejo | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 2022, First Round |
| 09.02.2022 | | Universidad César Vallejo | | Olimpia | | 0:1 (0:1) |
| Lima |
Copa Libertadores 2021, Group B |
| 26.05.2021 | | Olimpia | | Deportivo Táchira | | 6:2 (2:0) * |
| Asunción |
Copa Libertadores 2021, Group B |
| 13.05.2021 | | Always Ready | | Olimpia | | 1:2 (1:1) |
| La Paz |
Copa Libertadores 2021, Group B |
| 28.04.2021 | | Olimpia | | Always Ready | | 2:1 (0:0) * |
| Asunción |
Copa Libertadores 2020, Group G |
| 11.03.2020 | | Olimpia | | Defensa y Justicia | | 2:1 (0:0) |
| Asunción |
Copa Libertadores 2019, Group C |
| 09.04.2019 | | Olimpia | | Godoy Cruz | | 2:1 (2:0) |
| Asunción |
Copa Libertadores 2019, Group C |
| 04.04.2019 | | Sporting Cristal | | Olimpia | | 0:3 (0:0) |
| Lima |
Copa Libertadores 2018, Second qualifying stage |
| 01.02.2018 | | Olimpia | | Junior | | 1:0 (1:0) |
| Asunción |
Copa Libertadores 2018, First qualifying stage |
| 26.01.2018 | | Olimpia | | Montevideo Wanderers | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 2017, Third qualifying stage |
| 22.02.2017 | | Olimpia | | Botafogo | | 1:0 (0:0), pen. 1:3 |
| Asunción |
Copa Libertadores 2017, Second qualifying stage |
| 09.02.2017 | | Olimpia | | Independiente del Valle | | 3:1 (2:1) |
| Asunción |
Copa Libertadores 2016, Group 7 |
| 13.04.2016 | | Olimpia | | Deportivo Táchira | | 4:0 (2:0) |
| Asunción |
Copa Libertadores 2016, Group 7 |
| 17.03.2016 | | Olimpia | | Emelec | | 4:2 (1:1) |
| Asunción |
Copa Libertadores 2013, Final |
| 17.07.2013 | | Olimpia | | Atlético-MG | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 2013, Semifinal |
| 02.07.2013 | | Olimpia | | Santa Fe | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 2013, Quarterfinal |
| 29.05.2013 | | Olimpia | | Fluminense | | 2:1 (2:1) |
| Asunción |
Copa Libertadores 2013, Round of 16 |
| 16.05.2013 | | Olimpia | | Tigre | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 2013, Group 7 |
| 11.04.2013 | | Olimpia | | Newell's Old Boys | | 4:1 (1:0) |
| Asunción |
Copa Libertadores 2013, Group 7 |
| 04.04.2013 | | Universidad de Chile | | Olimpia | | 0:1 (0:0) |
| Santiago |
Copa Libertadores 2013, Group 7 |
| 13.03.2013 | | Deportivo Lara | | Olimpia | | 1:5 (0:3) |
| Barquisimeto |
Copa Libertadores 2013, Group 7 |
| 19.02.2013 | | Olimpia | | Universidad de Chile | | 3:0 (2:0) |
| Asunción |
Copa Libertadores 2013, Preliminary Round |
| 31.01.2013 | | Olimpia | | Defensor Sporting | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 2012, Group 2 |
| 28.03.2012 | | Olimpia | | Flamengo | | 3:2 (1:0) |
| Asunción |
Copa Libertadores 2012, Group 2 |
| 23.02.2012 | | Olimpia | | Lanús | | 2:1 (1:0) |
| Asunción |
Copa Libertadores 2004, Group 9 |
| 16.03.2004 | | Olimpia | | Sporting Cristal | | 2:1 (2:0) |
| Asunción |
Copa Libertadores 2003, Group 4 |
| 08.04.2003 | | Olimpia | | Gimnasia y Esgrima | | 4:1 (1:0) |
| Asunción |
Copa Libertadores 2003, Group 4 |
| 25.03.2003 | | Cobreloa | | Olimpia | | 2:3 (2:2) |
| Calama |
Copa Libertadores 2002, Final |
| 31.07.2002 | | São Caetano | | Olimpia | | 1:2 (1:0), pen. 2:4 |
| São Paulo |
Copa Libertadores 2002, Semifinal |
| 10.07.2002 | | Olimpia | | Grêmio | | 3:2 (1:1) |
| Asunción |
Copa Libertadores 2002, Quarterfinal |
| 16.05.2002 | | Olimpia | | Boca Juniors | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 2002, 1/8 finals |
| 02.05.2002 | | Olimpia | | Cobreloa | | 2:1 (2:0) |
| Asunción |
Copa Libertadores 2002, 1/8 finals |
| 23.04.2002 | | Cobreloa | | Olimpia | | 0:2 * |
| Calama |
Copa Libertadores 2002, Group 8 |
| 10.04.2002 | | Olimpia | | Flamengo | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 2002, Group 8 |
| 27.02.2002 | | Universidad Católica | | Olimpia | | 0:1 (0:1) |
| Santiago |
Copa Libertadores 2002, Group 8 |
| 21.02.2002 | | Olimpia | | Once Caldas | | 3:2 (2:2) |
| Asunción |
Copa Libertadores 2001, Group 4 |
| 22.02.2001 | | Olimpia | | Sporting Cristal | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 2000, Group 3 |
| 01.03.2000 | | Olimpia | | América Mexico | | 3:1 (2:1) |
| Asunción |
Copa Libertadores 2000, Group 3 |
| 22.02.2000 | | LDU | | Olimpia | | 0:1 (0:0) |
| Quito |
Copa Libertadores 1999, Group 3 |
| 05.03.1999 | | Olimpia | | Palmeiras | | 4:2 (0:1) |
| Asunción |
Copa Libertadores 1998, 1/8 finals |
| 29.04.1998 | | Olimpia | | Colón | | 1:0 (0:0), pen. 1:2 |
| Asunción |
Copa Libertadores 1998, Group 3 |
| 03.04.1998 | | Colo-Colo | | Olimpia | | 1:3 (0:2) |
| Santiago |
Copa Libertadores 1998, Group 3 |
| 18.03.1998 | | Cerro Porteño | | Olimpia | | 1:2 (1:0) |
| Asunción |
Copa Libertadores 1998, Group 3 |
| 06.03.1998 | | Olimpia | | Universidad Católica | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 1998, Group 3 |
| 25.02.1998 | | Olimpia | | Cerro Porteño | | 5:1 (2:0) |
| Asunción |
Copa Libertadores 1996, Group 1 |
| 12.04.1996 | | Olimpia | | Espoli | | 2:1 (0:0) |
| Asunción |
Copa Libertadores 1995, Group 2 |
| 04.04.1995 | | Olimpia | | Trujillanos | | 4:1 (2:0) |
| Asunción |
Copa Libertadores 1995, Group 2 |
| 03.03.1995 | | Caracas | | Olimpia | | 1:2 (0:2) |
| Caracas |
Copa Libertadores 1995, Group 2 |
| 21.02.1995 | | Olimpia | | Caracas | | 5:0 (2:0) |
| Asunción |
Copa Libertadores 1994, Semifinal |
| 17.08.1994 | | Olimpia | | São Paulo | | 1:0 (0:0), pen. 3:4 |
| Asunción |
Copa Libertadores 1994, Quarterfinal |
| 03.08.1994 | | Olimpia | | Bolívar | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 1994, Quarterfinal |
| 27.07.1994 | | Bolívar | | Olimpia | | 0:1 (0:0) |
| La Paz |
Copa Libertadores 1994, 1/8 finals |
| 27.04.1994 | | Olimpia | | Barcelona | | 2:1 (1:0) |
| Asunción |
Copa Libertadores 1994, 1/8 finals |
| 20.04.1994 | | Barcelona | | Olimpia | | 0:1 (0:1) |
| Guayaquil |
Copa Libertadores 1994, Group 1 |
| 12.04.1994 | | Olimpia | | Junior | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1994, Group 1 |
| 24.03.1994 | | Cerro Porteño | | Olimpia | | 1:3 (0:1) |
| Asunción |
Copa Libertadores 1994, Group 1 |
| 02.03.1994 | | Olimpia | | Cerro Porteño | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1993, 1/8 finals |
| 14.04.1993 | | Olimpia | | Nacional Montevideo | | 3:0 (0:0) |
| Asunción |
Copa Libertadores 1993, 1/8 finals |
| 07.04.1993 | | Nacional Montevideo | | Olimpia | | 1:2 (0:2) |
| Montevideo |
Copa Libertadores 1993, Group 5 |
| 10.03.1993 | | Olimpia | | Cerro Porteño | | 1:0 (1:0) |
| Asunción |
Copa Libertadores 1991, Semifinal |
| 23.05.1991 | | Olimpia | | Atlético Nacional | | 1:0 (1:0) |
| Asunción |
Copa Libertadores 1991, Quarterfinal |
| 08.05.1991 | | Olimpia | | Cerro Porteño | | 3:0 (1:0) |
| Asunción |
Copa Libertadores 1991, 1/8 finals |
| 26.04.1991 | | Olimpia | | Atlético Colegiales | | 2:1 (1:0) |
| Asunción |
Copa Libertadores 1990, Final |
| 03.10.1990 | | Olimpia | | Barcelona | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 1990, Semifinal |
| 20.09.1990 | | Atlético Nacional | | Olimpia | | 1:2 (1:1) |
| Chile, Santiago |
Copa Libertadores 1990, Quarterfinal |
| 22.08.1990 | | Olimpia | | Universidad Católica | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 1990, Group 5 |
| 03.04.1990 | | Olimpia | | Vasco da Gama | | 2:1 (1:1) |
| Asunción |
Copa Libertadores 1990, Group 5 |
| 27.03.1990 | | Olimpia | | Grêmio | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1990, Group 5 |
| 14.03.1990 | | Olimpia | | Cerro Porteño | | 2:1 (2:0) |
| Asunción |
Copa Libertadores 1989, Final |
| 24.05.1989 | | Olimpia | | Atlético Nacional | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 1989, Semifinal |
| 17.05.1989 | | Internacional | | Olimpia | | 2:3 (1:2), pen. 3:5 |
| Porto Alegre |
Copa Libertadores 1989, Quarterfinal |
| 19.04.1989 | | Olimpia | | Sol de América | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 1989, 1/8 finals |
| 05.04.1989 | | Olimpia | | Boca Juniors | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 1989, Group 1 |
| 23.03.1989 | | Olimpia | | Cobreloa | | 2:0 (2:0) |
| Asunción |
Copa Libertadores 1989, Group 1 |
| 10.03.1989 | | Olimpia | | Colo-Colo | | 2:0 |
| Asunción |
Copa Libertadores 1988, Group 4 |
| 26.08.1988 | | Olimpia | | Bolívar | | 4:2 (2:0) |
| Asunción |
Copa Libertadores 1988, Group 4 |
| 10.08.1988 | | Olimpia | | Cerro Porteño | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1987, First Round, Group 4 |
| 12.04.1987 | | Olimpia | | Barcelona | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1987, First Round, Group 4 |
| 01.04.1987 | | Olimpia | | El Nacional | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 1987, First Round, Group 4 |
| 15.03.1987 | | Olimpia | | Sol de América | | 2:1 (1:1) |
| Asunción |
Copa Libertadores 1986, Semifinal group 2 |
| 11.09.1986 | | Olimpia | | Bolívar | | 3:1 (0:1) |
| Asunción |
Copa Libertadores 1986, First Round, Group 5 |
| 13.08.1986 | | Nacional Asunción | | Olimpia | | 1:2 (1:1) |
| Asunción |
Copa Libertadores 1986, First Round, Group 5 |
| 07.08.1986 | | Olimpia | | Nacional Asunción | | 3:1 (3:1) * |
| Asunción |
Copa Libertadores 1984, First Round, Group 1 |
| 27.04.1984 | | Estudiantes La Plata | | Olimpia | | 0:1 (0:0) |
| La Plata |
Copa Libertadores 1984, First Round, Group 1 |
| 08.04.1984 | | Luqueño | | Olimpia | | 1:2 (1:2) * |
| Asunción |
Copa Libertadores 1984, First Round, Group 1 |
| 23.03.1984 | | Olimpia | | Estudiantes La Plata | | 2:1 (1:1) |
| Asunción |
Copa Libertadores 1984, First Round, Group 1 |
| 16.03.1984 | | Olimpia | | Independiente Avellaneda | | 1:0 (1:0) |
| Asunción |
Copa Libertadores 1982, Semifinal group 2 |
| 29.10.1982 | | Olimpia | | Deportes Tolima | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 1982, First Round, Group 5 |
| 25.04.1982 | | Olimpia | | Melgar | | 4:0 (2:0) |
| Asunción |
Copa Libertadores 1982, First Round, Group 5 |
| 18.04.1982 | | Olimpia | | Deportivo Municipal | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1982, First Round, Group 5 |
| 24.03.1982 | | Melgar | | Olimpia | | 0:3 (0:1) |
| Arequipa |
Copa Libertadores 1982, First Round, Group 5 |
| 20.03.1982 | | Deportivo Municipal | | Olimpia | | 1:2 (0:0) |
| Lima |
Copa Libertadores 1980, Semifinal group 2 |
| 10.07.1980 | | Olimpia | | O'Higgins | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 1980, Semifinal group 2 |
| 11.06.1980 | | O'Higgins | | Olimpia | | 0:1 (0:0) |
| Santiago |
Copa Libertadores 1979, Final |
| 22.07.1979 | | Olimpia | | Boca Juniors | | 2:0 (2:0) |
| Asunción |
Copa Libertadores 1979, Semifinal group 2 |
| 16.05.1979 | | Olimpia | | Palestino | | 3:0 (2:0) |
| Asunción |
Copa Libertadores 1979, Semifinal group 2 |
| 09.05.1979 | | Palestino | | Olimpia | | 0:2 (0:1) |
| Santiago |
Copa Libertadores 1979, Semifinal group 2 |
| 04.05.1979 | | Olimpia | | Guarani | | 2:1 (1:0) |
| Asunción |
Copa Libertadores 1979, First Round, Group 2 |
| 18.04.1979 | | Olimpia | | Bolívar | | 3:0 (2:0) |
| Asunción |
Copa Libertadores 1979, First Round, Group 2 |
| 08.04.1979 | | Olimpia | | Jorge Wilstermann | | 4:2 (3:0) |
| Asunción |
Copa Libertadores 1979, First Round, Group 2 |
| 05.04.1979 | | Sol de América | | Olimpia | | 0:1 (0:0) |
| Asunción |
Copa Libertadores 1979, First Round, Group 2 |
| 29.03.1979 | | Jorge Wilstermann | | Olimpia | | 0:2 (0:1) |
| Cochabamba |
Copa Libertadores 1979, First Round, Group 2 |
| 23.03.1979 | | Olimpia | | Sol de América | | 2:1 (1:1) |
| Asunción |
Copa Libertadores 1977, First Round, Group 4 |
| 29.04.1977 | | Olimpia | | Universidad de Chile | | 1:0 (1:0) |
| Asunción |
Copa Libertadores 1976, First Round, Group 3 |
| 28.03.1976 | | Luqueño | | Olimpia | | 0:1 (0:0) |
| Asunción |
Copa Libertadores 1975, First Round, Group 1 |
| 21.03.1975 | | Olimpia | | Cerro Porteño | | 2:1 (2:1) |
| Asunción |
Copa Libertadores 1975, First Round, Group 1 |
| 07.03.1975 | | Olimpia | | Newell's Old Boys | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 1974, First Round, Group 5 |
| 05.03.1974 | | Olimpia | | Nacional Montevideo | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 1973, First Round, Group 5 |
| 16.03.1973 | | Olimpia | | Sporting Cristal | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1973, First Round, Group 5 |
| 09.03.1973 | | Olimpia | | Universitario de Deportes | | 3:1 (0:0) |
| Asunción |
Copa Libertadores 1973, First Round, Group 5 |
| 02.03.1973 | | Olimpia | | Cerro Porteño | | 2:1 (1:0) |
| Asunción |
Copa Libertadores 1972, First Round, Group 3 |
| 09.03.1972 | | Cerro Porteño | | Olimpia | | 1:3 (1:1) |
| Asunción |
Copa Libertadores 1970, First Round, Group 3 |
| 21.03.1970 | | Olimpia | | Deportivo Cali | | 5:1 (3:1) |
| Asunción |
Copa Libertadores 1970, First Round, Group 3 |
| 15.03.1970 | | Olimpia | | América de Cali | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1970, First Round, Group 3 |
| 05.03.1970 | | Deportivo Cali | | Olimpia | | 0:1 (0:1) |
| Santiago de Cali |
Copa Libertadores 1970, First Round, Group 3 |
| 18.02.1970 | | Olimpia | | Rangers | | 5:1 |
| Asunción |
Copa Libertadores 1969, First Round, Group 3 |
| 18.03.1969 | | Olimpia | | Bolívar | | 2:1 aet (0:0, 1:1) * |
| Argentina, Avellaneda |
Copa Libertadores 1969, First Round, Group 3 |
| 14.03.1969 | | Olimpia | | Litoral | | 2:0 (0:0) |
| Asunción |
Copa Libertadores 1969, First Round, Group 3 |
| 07.03.1969 | | Olimpia | | Bolívar | | 4:0 (1:0) |
| Asunción |
Copa Libertadores 1969, First Round, Group 3 |
| 09.02.1969 | | Litoral | | Olimpia | | 0:3 (0:2) |
| Cochabamba |
Copa Libertadores 1966, First Round, Group 2 |
| 16.03.1966 | | Olimpia | | Universidad de Chile | | 2:0 (1:0) |
| Asunción |
Copa Libertadores 1966, First Round, Group 2 |
| 05.03.1966 | | Universidad de Chile | | Olimpia | | 1:2 (0:1) |
| Santiago |
Copa Libertadores 1963, Group 3 |
| 24.07.1963 | | Olimpia | | Universidad de Chile | | 2:1 (1:0) |
| Asunción |
Copa Libertadores 1963, Group 3 |
| 07.04.1963 | | Olimpia | | Boca Juniors | | 1:0 (0:0) |
| Asunción |
Copa Libertadores 1961, Quarterfinal |
| 09.04.1961 | | Colo-Colo | | Olimpia | | 2:5 (1:2) |
| Santiago |
Copa Libertadores 1960, Semifinal |
| 05.06.1960 | | Olimpia | | Los Millonarios | | 5:1 (2:0) |
| Asunción |