1968–69 Taça de Portugal
The 1968–69 Taça de Portugal was the 29th edition of the Portuguese football knockout tournament, organized by the Portuguese Football Federation. The 1968–69 Taça de Portugal began on September 1968. The final was played on 22 June 1969 at the Estádio Nacional.
Porto were the previous holders, having defeated Vitória de Setúbal 2–1 in the previous season's final. Defending champions Porto were unable to regain the Taça de Portugal as they were defeated in the fourth round by eventual winners Benfica, who went on to defeat Académica de Coimbra in the final and claim their thirteenth Taça de Portugal.
First round
Teams from the Portuguese Second Division and the Portuguese Third Division entered at this stage. Due to the expansion of third tier teams being able to participate in the competition, two legged first round cup ties were scrapped. First round ties which ended in a draw, were replayed at a later date.| Home team | Score | Away team |
| Alhandra | Odivelas | |
| Barreirense | Oliveirense | |
| Beira-Mar | União de Coimbra | |
| Celoricense | Mortágua | |
| Desportivo das Aves | Torres Novas | |
| Desportivo de Beja | Gil Vicente | |
| Estrela de Portalegre | Almada | |
| Fafe | Oriental | |
| Famalicão | Académico de Viseu | |
| Farense | Salgueiros | |
| Feirense | São Pedro da Cova | |
| Ferroviários | União de Montemor | |
| Guarda | Seixal | |
| Juventude de Évora | Casa Pia | |
| Leões Santarém | Marialvas | |
| Lusitano de Évora | Faro e Benfica | |
| Marinhense | Gouveia | |
| Montijo | Cova da Piedade | |
| Naval | Bragança |
| Home team | Score | Away team |
| Nazarenos | Aljustrelense | |
| O Grandolense | Sporting de Lamego | |
| Olhanense | Sporting de Espinho | |
| Penafiel | Leça | |
| Peniche | Lusitano VRSA | |
| Portimonense | Sesimbra | |
| Sacavenense | Chaves | |
| Sintrense | Torreense | |
| Sporting da Covilhã | Pinhelenses | |
| Tirsense | Riopele | |
| Tramagal | Desportivo de Castelo Branco | |
| União de Algés | Sarilhense | |
| União de Almeirim | Lusitano FCV | |
| União de Lamas | Luso | |
| União de Leiria | Lusitânia Lourosa | |
| Vasco da Gama Sines | Rio Ave | |
| Vianense | Boavista | |
| Vila Real | Mirandela | |
| Vizela | Valecambrense |
Replays
| Home team | Score | Away team |
| Alhandra | Odivelas | |
| Desportivo das Aves | Torres Novas | |
| Desportivo de Beja | Gil Vicente | |
| Estrela de Portalegre | Almada |
| Home team | Score | Away team |
| Naval | Bragança | |
| Penafiel | Leça | |
| Riopele | Tirsense | |
| União de Algés | Sarilhense |
Second round
| Home team | Score | Away team |
| Barreirense | Alhandra | |
| Beira-Mar | Sporting da Covilhã | |
| Celoricense | Vizela | |
| Desportivo das Aves | Vianense | |
| Desportivo de Beja | União de Algés | |
| Fafe | União de Lamas | |
| Famalicão | Vasco da Gama Sines | |
| Farense | Ferroviários | |
| Feirense | Estrela de Portalegre | |
| Guarda | Tirsense |
| Home team | Score | Away team |
| Lusitano de Évora | Nazarenos | |
| Montijo | Sintrense | |
| Olhanense | Juventude de Évora | |
| Portimonense | O Grandolense | |
| Sacavenense | Marinhense | |
| Tramagal | Naval | |
| União de Almeirim | Leões Santarém | |
| União de Leiria | Penafiel | |
| Vila Real | Peniche |
Replays
| Home team | Score | Away team |
| União de Lamas | Fafe |
Third round
Due to a lack of teams involved in the fourth round, the organizing body of the competition, the Portuguese Football Federation, decided to have an additional round where the teams who lost their second round ties would be given a second opportunity to progress to the next round of the competition.| Home team | Score | Away team |
| Alhandra | União de Algés | |
| Estrela de Portalegre | Guarda | |
| Fafe | Naval | |
| Ferroviários | Juventude de Évora | |
| Marinhense | Portimonense |
| Home team | Score | Away team |
| Nazarenos | Vila Real | |
| Penafiel | Leões Santarém | |
| Vasco da Gama Sines | Sintrense | |
| Vianense | Celoricense |
Replays
| Home team | Score | Away team |
| Alhandra | União de Algés |
| Home team | Score | Away team |
| Penafiel | Leões Santarém |
Fourth round
Ties were played between on the 9 February. Teams from the Primeira Liga entered at this stage.| Home team | Score | Away team |
| Académica de Coimbra | Farense | |
| Atlético CP | Braga | |
| Beira-Mar | Varzim | |
| Belenenses | Sacavenense | |
| Benfica | União de Almeirim | |
| Desportivo das Aves | Sporting CP | |
| Desportivo de Beja | Vianense | |
| Estrela de Portalegre | Leões Santarém | |
| Feirense | Sanjoanense | |
| Ferroviários | Vizela | |
| Leixões | Alhandra |
| Home team | Score | Away team |
| Montijo | Vitória de Setúbal | |
| Nazarenos | Lusitano de Évora | |
| Olhanense | Tramagal | |
| Peniche | Vitória de Guimarães | |
| Porto | Fafe | |
| Sintrense | Famalicão | |
| Tirsense | Marinhense | |
| União de Lamas | Fabril Barreiro | |
| União de Leiria | Barreirense | |
| União de Tomar | O Grandolense |
Replays
| Home team | Score | Away team |
| Vitória de Guimarães | Peniche |
Fifth round
Ties were played between on the 9 March. Due to the odd number of teams involved at this stage of the competition, Sporting CP qualified for the next round due to having no opponent to face at this stage of the competition.| Home team | Score | Away team |
| Barreirense | Atlético CP | |
| Benfica | Porto | |
| Desportivo de Beja | União de Tomar | |
| Fabril Barreiro | Nazarenos | |
| Leixões | Olhanense |
| Home team | Score | Away team |
| Leões Santarém | Académica de Coimbra | |
| Tirsense | Sanjoanense | |
| Varzim | Famalicão | |
| Vitória de Setúbal | Belenenses | |
| Vizela | Vitória de Guimarães |