코파 이탈리아 2019-20
First stage > 2회전

1회전 승자들과 세리에 B에서 총 40개팀들이 이 2회전에서 시작한다., 이 중 승자 20개팀들이 세리에 A에서 12개팀들과 함께 3회전에 진출한다.
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| 10 August 2019 | Ascoli (2) | 5–1  | Pro Vercelli (3) | Stadio Cino e Lillo Del Duca |   |  |
| 18:30 CEST (UTC+02:00) |  Brosco  7′  da Cruz  20′  Ardemagni  54′ (페널티)  Scamacca  72′, 87′  | 리포트 |  Azzi  33′  |     |   |  |

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| 11 August 2019 | Spezia (2) | 5–0  | Pro Patria (3) | Stadio Alberto Picco |   |  |
| 18:00 CEST (UTC+02:00) |  Gyasi  15′  Guðjohnsen  25′  F. Ricci  53′  M. Ricci  64′  Burgzorg  90+2′  |  |  |     |   |  |

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| 11 August 2019 | Perugia (2) | 1–0  | Triestina (3) | Stadio Renato Curi |   |  |
| CEST (UTC+02:00) |  Sgarbi  28′  |  |  |     |   |  |

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| 11 August 2019 | Cremonese (2) | 4–0  | Virtus Francavilla (3) | Stadio Giovanni Zini |   |  |
| CEST (UTC+02:00) |  Claiton  41′  Deli  44′  Palombi  58′, 66′  |  |  |     |   |  |

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| 11 August 2019 | Empoli (2) | 2–1  | Reggina (3) | Stadio Carlo Castellani |   |  |
| CEST (UTC+02:00) |  Mancuso  22′  Antonelli  72′  |  |  Corazza  28′  |     |   |  |

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| 11 August 2019 | Pescara (2) | 3–2  | Mantova (4) | Stadio Adriatico – Giovanni Cornacchia |   |  |
| CEST (UTC+02:00) |  Tumminello  13′ (페널티)  Di Grazia  79′  Ventola   |  |  Guccione  50′  Tremolada  90′  |     |   |  |

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| 11 August 2019 | Benevento (2) | 3–4  | Monza (3) | Stadio Ciro Vigorito |   |  |
| CEST (UTC+02:00) |  Tello  51′, 83′  Viola  90+4′ (페널티)  |  |  Bellusci  4′  Finotto  17′, 88′  Iocolano  49′  |     |   |  |

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| 11 August 2019 | Livorno (2) | 0–1  | Carpi (3) | Stadio Armando Picchi |   |  |
| CEST (UTC+02:00) |  |  |  Vano  69′  |     |   |  |

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| 11 August 2019 | Cittadella (2) | 3–0  | Padova (3) | Stadio Pier Cesare Tombolato |   |  |
| CEST (UTC+02:00) |  Iori  23′ (페널티)  Diaw  26′  Celar  87′  |  |  |     |   |  |

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| 11 August 2019 | Chievo (2) | 1–1  | Ravenna (3) | Stadio Marc'Antonio Bentegodi |   |  |
| CEST (UTC+02:00) |  Meggiorini  23′  |  |  Raffini  62′  |     |   |  |

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| 11 August 2019 | Crotone (2) | 4–3  | Arezzo (3) | Stadio Ezio Scida |   |  |
| CEST (UTC+02:00) |  Barberis  2′  Simy  7′  Golemić  33′  Ruggiero  75′  |  |  Borghini  10′  Belloni  17′ (페널티)  Zini   |     |   |  |

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| 11 August 2019 | Pordenone (2) | 1–2  | Feralpisalò (3) | Stadio Ottavio Bottecchia |   |  |
| CEST (UTC+02:00) |  Pobega  44′  |  |  Ceccarelli  30′  Scarsella  50′  |     |   |  |

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| 11 August 2019 | Juve Stabia (2) | 1–1  | Imolese (3) | Stadio Romeo Menti |   |  |
| 19:45 CEST (UTC+02:00) |  Carlini  60′ (페널티)  |  |  Vuthaj  66′  |     |   |  |

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| 11 August 2019 | Trapani (2) | 3–1  | Piacenza (3) | Stadio Polisportivo Provinciale |   |  |
| CEST (UTC+02:00) |  Evacuo  44′, 59′  Nzola  82′  |  |  Cacia  12′  |     |   |  |

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| 11 August 2019 | Venezia (2) | 2–1  | Catania (3) | Stadio Pierluigi Penzo |   |  |
| 19:00 CEST (UTC+02:00) |  Aramu  3′  Zuculini  56′  |  |  Silvestri  41′  |     |   |  |

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| 11 August 2019 | Frosinone (2) | 4–0  | Carrarese (3) | Stadio Benito Stirpe |   |  |
| 20:30 CEST (UTC+02:00) |  Cian0  10′  Paganini  43′  Ariaudo  49′  Tribuzzi  81′  |  |  |     |   |  |

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| 11 August 2019 | Monopoli (3) | 1–0  | Cosenza (2) | Stadio Vito Simone Veneziani |   |  |
| 20:30 CEST (UTC+02:00) |  Mendicino  89′ (페널티)  |  |  |     |   |  |

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| 11 August 2019 | Virtus Entella (2) | 1–2  | Südtirol (3) | Stadio Comunale |   |  |
| 20:30 CEST (UTC+02:00) |  Paolucci  26′  |  |  Casiraghi  8′  Morosini  84′  |     |   |  |

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| 11 August 2019 | Pisa (2) | 3–0  | Potenza (3) | Arena Garibaldi – Stadio Romeo Anconetani |   |  |
| 20:45 CEST (UTC+02:00) |  Marconi  43′  Masucci  53′  Aya  71′  |  |  |     |   |  |

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| 11 August 2019 | Salernitana (2) | 3–1  | Catanzaro (3) | Stadio Arechi |   |  |
| 20:45 CEST (UTC+02:00) |  Kiyine  22′ (페널티)  Giannetti  45′, 73′  |  |  Mangni  79′  |     |   |  |