Piala Italia 2020–2021
Tahap pertama > Babak pertama

Sebanyak 36 tim dari Serie C dan Serie D bertanding di babak ini, delapan belas di antaranya melaju ke babak kedua.
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| 22 September 2020 | Südtirol (3) | 2–1 | Latte Dolce (4) | Salò |  |
| 14:30 CEST (UTC+2) |  Rover  29'  Polák  34'  | Laporan |  Bianchi  90+3'  | Stadion: Stadio Lino Turina  Penonton: 0 Wasit: Giacomo Camplone  |     |
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| 22 September 2020 | Ternana (3) | 1–2 | AlbinoLeffe (3) | Terni |  |
| 20:30 CEST (UTC+2) |  Partipilo  50'  | Laporan |  Cori  40'  Canestrelli  44'  | Stadion: Stadio Libero Liberati  Penonton: 0 Wasit: Francesco Fourneau  |     |
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| 23 September 2020 | Piacenza (3) | 1–2 | Teramo (3) | Piacenza |  |
| 15:30 CEST (UTC+2) |  Bruzzone  22'  | Laporan |  Santoro  5'  Pinzauti  23'  | Stadion: Stadio Leonardo Garilli  Penonton: 0 Wasit: Antonio Rapuano  |     |
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| 23 September 2020 | Carpi (3) | 1–3 (p.w.) | Casarano (4) | Carpi |  |
| 16:00 CEST (UTC+2) |  Giovannini  74'  | Laporan |  Rodríguez  5', 105'  Sansone  100'  | Stadion: Stadio Sandro Cabassi  Penonton: 0 Wasit: Alessandro Prontera  |     |
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| 23 September 2020 | Alessandria (3) | 3–2 | Sambenedettese (3) | Alessandria |  |
| 16:30 CEST (UTC+2) |  Eusepi  13', 17'  Arrighini  90' (pen.)  | Laporan |  Nocciolini  25'  Panaioli  90+4'  | Stadion: Stadio Giuseppe Moccagatta  Penonton: 0 Wasit: Lorenzo Maggioni  |     |
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| 23 September 2020 | Novara (3) | 3–1 | Gelbison (4) | Novara |  |
| 16:30 CEST (UTC+2) |  Schiavi  21', 39' (pen.)  Buzzegoli  48'  | Laporan |  Coulibaly  7'  | Stadion: Stadio Silvio Piola  Penonton: 0 Wasit: Simone Sozza  |     |
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| 23 September 2020 | Carrarese (3) | 4–0 | Ambrosiana (4) | Carrara |  |
| 17:00 CEST (UTC+2) |  Infantino  2'  Schirò  7'  Rota  9'  Caccavallo  86'  | Laporan |  | Stadion: Stadio dei Marmi  Penonton: 0 Wasit: Manuel Volpi  |     |
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| 23 September 2020 | Catanzaro (3) | 2–1 | Virtus Francavilla (3) | Catanzaro |  |
| 17:00 CEST (UTC+2) |  Casoli  35'  Carlini  45' (pen.)  | Laporan |  Franco  32'  | Stadion: Stadio Nicola Ceravolo  Penonton: 0 Wasit: Valerio Marini  |     |
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| 23 September 2020 | Livorno (3) | 1–2 | Pro Patria (3) | Livorno |  |
| 17:00 CEST (UTC+2) |  Gonnelli  81'  | Laporan |  Parker  17'  Latte Lath  49'  | Stadion: Stadio Armando Picchi  Penonton: 0 Wasit: Francesco Meraviglia  |     |
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| 23 September 2020 | Pontedera (3) | 1–2 | Arezzo (3) | Piancastagnaio |  |
| 17:00 CEST (UTC+2) |  Piana  67'  | Laporan |  Belloni  52'  Cutolo  90+4'  | Stadion: Stadio Comunale  Penonton: 0 Wasit: Daniele Paterna  |     |
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| 23 September 2020 | Bari (3) | 4–0 | Trastevere (4) | Bari |  |
| 17:30 CEST (UTC+2) |  D'Ursi  15'  Marras  23'  Antenucci  36'  Candellone  75'  | Laporan |  | Stadion: Stadio San Nicola  Penonton: 0 Wasit: Luca Massimi  |     |
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| 23 September 2020 | Juve Stabia (3) | 2–1 | Tritium (4) | Castellammare di Stabia |  |
| 18:00 CEST (UTC+2) |  Aldè  45' (b.d.)  Mastalli  87'  | Laporan |  Marzeglia  81'  | Stadion: Stadio Romeo Menti  Penonton: 0 Wasit: Matteo Marchetti  |     |
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| 23 September 2020 | Renate (3) | 2–1 | Avellino (3) | Meda |  |
| 18:00 CEST (UTC+2) |  Giovinco  10'  Galuppini  74'  | Laporan |  Burgio  83'  | Stadion: Stadio Città di Meda  Penonton: 0 Wasit: Matteo Gariglio  |     |
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| 23 September 2020 | Feralpisalò (3) | 1–0 | Pineto (4) | Salò |  |
| 18:30 CEST (UTC+2) |  Ceccarelli  36'  | Laporan |  | Stadion: Stadio Lino Turina  Penonton: 0 Wasit: Daniel Amabile  |     |
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| 23 September 2020 | Potenza (3) | 0–2 | Triestina (3) | Potenza |  |
| 18:30 CEST (UTC+2) |  | Laporan |  Maracchi  19'  Di Massimo  28'  | Stadion: Stadio Alfredo Viviani  Penonton: 212 Wasit: Lorenzo Illuzzi  |     |
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| 23 September 2020 | Padova (3) | 2–0 | Breno (4) | Padua |  |
| 19:00 CEST (UTC+2) |  Santini  13'  Ronaldo  74'  | Laporan |  | Stadion: Stadio Euganeo  Penonton: 0 Wasit: Federico Dionisi  |     |
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| 23 September 2020 | Monopoli (3) | 1–0 | Modena (3) | Monopoli |  |
| 20:00 CEST (UTC+2) |  Paolucci  77'  | Laporan |  | Stadion: Stadio Vito Simone Veneziani  Penonton: 0 Wasit: Ivano Pezzuto  |     |
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| 23 September 2020 | Catania (3) | 1–2 (p.w.) | San Nicolò Notaresco (4) | Catania |  |
| 20:45 CEST (UTC+2) |  Biondi  27'  | Laporan |  Speranza  56'  Cancelli  99'  | Stadion: Stadio Angelo Massimino  Penonton: 0 Wasit: Alberto Santoro  |     |