Third round
| 17 October 2019 | Alverca (CP) | 2-0 Alex, Luan | (I) Sporting CP |
|---|---|---|---|
| 18 October 2019 | Cova da Piedade (II) | 0-4 Pizzi (2), Carlos Vinicius (2) | (I) Benfica |
| 19 October 2019 | Condeixa (CP) | 0-1 Nuno Santos | (I) Rio Ave |
| 19 October 2019 | Sintra Football (CP) | 1-1 Elvis / Davidson (4-3 pen.) | (I) Vitória de Guimarães |
| 19 October 2019 | Louletano (CP) | 1-2 Brico Castro / Dadashov, Helder Ferreira | (I) Paços de Ferreira |
| 19 October 2019 | Fabril Barreiro (CP) | 1-3 Celestino / Pedro Nuno (2), Fabio Abreu | (I) Moreirense |
| 19 October 2019 | Pevidém (D) | 0-2 Robinho, Lica | (I) Belenenses SAD |
| 19 October 2019 | Amora (CP) | 0-1 Belkheir | (CP) Sanjoanense |
| 19 October 2019 | Espinho (CP) | 2-1 Joo Pinto, Miguel Baptista / Dnis Martins | (II) Vilafranquense |
| 19 October 2019 | Académico Viseu (II) | 3-1 Jean Patric, Fernando Ferreira, Jean Patric / Juan San Martin | (CP) Real |
| 19 October 2019 | Penafiel (II) | 0-2 Sandro Lima, Claude Goncalves | (I) Gil Vicente |
| 19 October 2019 | Feirense (II) | 3-0 Fabio Espinho, Enca Fati, Christian | (I) Tondela |
| 19 October 2019 | Farense (II) | 5-2 Fabricio Simes (3), Cassio Scheid, Dawigala / Welinton Junior (2) | (I) Aves |
| 19 October 2019 | Académica (II) | 2-1 Hwang Mun-Ki, Djouss / Jackson Martinez | (I) Portimonense |
| 19 October 2019 | Coimbrões (CP) | 0-5 Luis Diaz (2), Tiquinho Soares, Mbemba, Fabio Silva | (I) Porto |
| 19 October 2019 | Leça (CP) | 1-3 Adilson Silva / Wilson Eduardo (2), Ricardo Horta | (I) Braga |
| 20 October 2019 | Águias do Moradal (D) | 0-5 Nabil Ghilas (3), Carlinhos, Zequinha | (I) Vitória de Setúbal |
| 20 October 2019 | Mafra (II) | 1-0 Ruben Freitas | (CP) Fafe |
| 20 October 2019 | Varzim (II) | 1-0 Leonardo Ruiz | (II) Estoril |
| 20 October 2019 | Lusitânia (CP) | 1-1 Goba Zakpa / Anderson Oliveira (5-6 pen.) | (I) Famalicão |
| 20 October 2019 | AD Oliveirense (CP) | 0-3 Thiago Santana, Bruno Lamas, Joo Afonso | (I) Santa Clara |
| 20 October 2019 | Vitória de Sernache (CP) | 0-0 (4-5 pen.) | (CP) Sertanense |
| 20 October 2019 | Marinhense (CP) | 1-0 Ednilson Furtado | (CP) Fátima |
| 20 October 2019 | Loures (CP) | 4-2 Bruno Bernardo, Hugo Machado (2), Rafael Batatinha / Stevy Okitokandjo, Rafa Pinto | (CP) Benfica Castelo Branco |
| 20 October 2019 | Olímpico Montijo (CP) | 0-1 Nadson | (CP) Anadia |
| 20 October 2019 | Casa Pia (II) | 1-3 Wilson Kenidy / Francis Okoli, Samu, Diogo Ribeiro | (CP) Vizela |
| 20 October 2019 | Arouca (CP) | 1-0 Valdu T | (CP) Merelinense |
| 20 October 2019 | Pedras Salgadas (CP) | 1-0 Marcelo | (CP) Águeda |
| 20 October 2019 | Chaves (II) | 2-1 Andre Luis, Kevin Medina / Alberto Bueno | (I) Boavista |
| 20 October 2019 | Valadares Gaia (CP) | 0-0 (10-11 pen.) | (CP) Canelas 2010 |
| 20 October 2019 | Beira-Mar (CP) | 2-2 Joo Nogueira, Isaac Ciss / Daizen Maeda, Zainadine Junior (5-4 pen.) | (I) Marítimo |
| 20 October 2019 | Leixões (II) | 4-2 Junior Sena, Pedro Pinto, Andre Claro, Bruno Braga / Filipe Andrade, Matheus Souza | (CP) Praiense |
Fourth round
| 22 November 2019 | Leixões (II) | 1–4 Pedro Pinto / Ze Manuel, Osama Rashid, Carlos Carvalho (2) | (I) Santa Clara |
|---|---|---|---|
| 22 November 2019 | Varzim (II) | 1–0 Levi Lumeka | (CP) Loures |
| 23 November 2019 | Sertanense (CP) | 2–1 Paulo Marquinhos, Rafael Vieira / Fabricio Simes | (II) Farense |
| 23 November 2019 | Académico Viseu (II) | 1–0 Fall | (II) Feirense |
| 24 November 2019 | Espinho (CP) | 3–2 Vieirinha 22' Joo Silva, Diogo Valente / Benny Silvano, Deo | (CP) Arouca |
| 23 November 2019 | Famalicão (I) | 1–0 Toni Martinez | (II) Académica |
| 23 November 2019 | Braga (I) | 1–0 Ricardo Horta | (I) Gil Vicente |
| 23 November 2019 | Vizela (CP) | 1–2 Samu / Raul De Tomas, Carlos Vinicius | (I) Benfica |
| 24 November 2019 | Moreirense (I) | 1–3 Fabio Abreu / Medeiros (2), Joel | (II) Mafra |
| 24 November 2019 | Sintra Football (CP) | 0–2 Leandro Miguel Curto Antunes (2) | (CP) Marinhense |
| 24 November 2019 | Paços de Ferreira (I) | 1–0 Mohamed Diaby | (CP) Sanjoanense |
| 24 November 2019 | Pedras Salgadas (CP) | 0–0 (6-7 p) | (CP) Canelas 2010 |
| 24 November 2019 | Anadia (CP) | 2–1 Tiago Borges, Rui Rainho / Fabio da Rocha Vieira | (CP) Beira-Mar |
| 24 November 2019 | Rio Ave (I) | 1–0 Filipe Augusto | (CP) Alverca |
| 24 November 2019 | Porto (I) | 4–0 Jubal (og), Moussa Marega, Fabio Silva, Chancel Mbemba | (I) Vitória de Setúbal |
| 24 November 2019 | Chaves (II) | 1–0 Andre Luis | (I) Belenenses SAD |
1/8 round
| Date | Host Team | Score | Away Team |
|---|---|---|---|
| 18-12-2019 | Académico Viseu (II) | 1-0 Joao Mario | Chaves (II) |
| 18-12-2019 | Varzim (II) | 2-1 Leonardo Ruiz, Baba Sow / Ruben Silvestre | Anadia (CP) |
| 18-12-2019 | Benfica (I) | 2-1 Pizzi, Carlos Vinicius / Ferro (og) | Braga (I) |
| 18-12-2019 | Famalicão (I) | 3-0 Pedro Gonçalves, Diogo Gonçalves, Toni Martinez | (II) Mafra |
| 18-12-2019 | FC Porto (I) | 1-0 Shoya Nakajima | (I) Santa Clara |
| 18-12-2019 | Paços de Ferreira (I) | 3-0 Pedrinho, Murilo Oliveira de Freitas (2) | Espinho (CP) |
| 18-12-2019 | (CP) Marinhense | 0-2 Tarantini, Ronan | Rio Ave (I) |
| 18-12-2019 | Sertanense (CP) | 0-1 Baba Zakaria | (CP) Canelas 2010 |
Quarters Finals
| Date | Host Team | Score | Away Team |
|---|---|---|---|
| 14-01-2020 | FC Porto | 2-1 Soares Tiquinho, Ivan Marcano / Hugo Gomes | Varzim S.C. |
| 14-01-2020 | SL Benfica | 3-2 Franco Cervi, Haris Seferovic (2) / Lucas Piazon, Mehdi Taremi | Rio Ave |
| 15-01-2020 | Paços de Ferreira | 0-1 Diogo Goncalves | Famalicão |
| 15-01-2020 | Académico de Viseu | 1-0 Anthony Charles Carter | Canelas 2010 |
Semis Finals
| 04-02-2020 | Academico de Viseu | 1-1 Joao Mario / Ze Luis | FC Porto |
| 12-02-2020 | FC Porto | 3-0 Alex Telles, Luis Ze, Sergio Oliveira | Academico de Viseu |
| 04-02-2020 | SL Benfica | 3-2 Pizzi, Rafa Silva, Gabriel Appelt Pires / Pedro Gonçalves, Toni Martinez | FC Famalicao |
| 11-02-2020 | FC Famalicao | 1-1 Toni Martinez / Pizzi | SL Benfica |
Final
| Date | Stadium, Venue | Team 1 | Score | Team 2 |
| 01-08-2020 | Estádio Cidade de Coimbra, Coimbra | FC Poto | 2-1 Chancel Mbemba (2) / Carlos Vinícius | SL Benfica |