Piala Italia 2020–2021
Tahap pertama > Babak kedua

Sebanyak empat puluh tim (delapan belas pemenang dari babak pertama, dua dari Serie C, dan dua puluh dari Serie B) berkompetisi di babak kedua, dua puluh di antaranya melaju ke babak ketiga.
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| 29 September 2020 | Monza (2) | 3–0 | Triestina (3) | Monza |  |
| 20:45 CEST (UTC+2) |  Barillà  23'  Offredi  77' (b.d.)  Machín  90' (pen.)  | Laporan |  | Stadion: Stadio Brianteo  Penonton: 439 Wasit: Marco Serra  |     |
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| 30 September 2020 | Reggina (2) | 1–0 | Teramo (3) | Reggio Calabria |  |
| 14:00 CEST (UTC+2) |  Di Chiara  34'  | Laporan |  | Stadion: Stadio Oreste Granillo  Wasit: Antonio Santoro  |     |
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| 30 September 2020 | Cittadella (2) | 3–1 | Novara (3) | Cittadella |  |
| 15:00 CEST (UTC+2) |  Iori  16' (pen.)  Rosafio  74'  Ogunseye  79'  | Laporan |  Panico  76'  | Stadion: Stadio Pier Cesare Tombolato  Wasit: Eugenio Abbattista  |     |
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| 30 September 2020 | Cosenza (2) | 0–0 (p.w.) (3–1 a.p.) | Alessandria (3) | Cosenza |  |
| 15:00 CEST (UTC+2) |  | Laporan |  | Stadion: Stadio San Vito-Gigi Marulla  Wasit: Ivano Pezzuto  |  |
|   |   | Adu penalti |  |  |  |
|   |  Carretta   Idda   Kone   |   |   Casarini   Arrighini   Castellano   Di Quinzio  |  |  |
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| 30 September 2020 | Cremonese (2) | 4–0 | Arezzo (3) | Cremona |  |
| 15:00 CEST (UTC+2) |  Ceravolo  61'  Fiordaliso  81'  Gaetano  90+1', 90+2'  | Laporan |  | Stadion: Stadio Giovanni Zini  Penonton: 0 Wasit: Gianluca Manganiello  |     |
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| 30 September 2020 | Frosinone (2) | 1–3 | Padova (3) | Frosinone |  |
| 15:00 CEST (UTC+2) |  Tabanelli  20'  | Laporan |  Della Latta  21', 44'  Soleri  34'  | Stadion: Stadio Benito Stirpe  Wasit: Giacomo Camplone  |     |
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| 30 September 2020 | Pisa (2) | 2–0 | Juve Stabia (3) | Pisa |  |
| 15:00 CEST (UTC+2) |  Sibilli  7', 50' (pen.)  | Laporan |  | Stadion: Arena Garibaldi – Stadio Romeo Anconetani  Wasit: Valerio Marini  |     |
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| 30 September 2020 | Pescara (2) | 1–1 (p.w.) (8–7 a.p.) | San Nicolò Notaresco (4) | Pescara |  |
| 15:30 CEST (UTC+2) |  Riccardi  25'  | Laporan |  Banegas  34'  | Stadion: Stadio Adriatico – Giovanni Cornacchia  Wasit: Antonio Di Martino  |  |
|   |   | Adu penalti |  |  |  |
|   |  Maistro   Memushaj   Capone   Ceter   Galano   Bellanova   Ventola   Omeonga   Jaroszyński   Scognamiglio   |   |   Frulla   Cesario   Cancelli   Bianciardi   Banegas   Colombatti   Lattarulo   Blando   Gallo   Sorrini  |  |  |
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| 30 September 2020 | Virtus Entella (2) | 2–1 | AlbinoLeffe (3) | Chiavari |  |
| 16:00 CEST (UTC+2) |  Koutsoupias  30'  Petrovic  38'  | Laporan |  Gușu  90+2'  | Stadion: Stadio Comunale  Wasit: Matteo Gariglio  |     |
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| 30 September 2020 | Ascoli (2) | 1–4 | Perugia (3) | Ascoli Piceno |  |
| 17:00 CEST (UTC+2) |  Ghazoini  89'  | Laporan |  Rosi  12'  Murano  24'  Dragomir  42'  Lunghi  46'  | Stadion: Stadio Cino e Lillo Del Duca  Wasit: Luca Massimi  |     |
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| 30 September 2020 | Empoli (2) | 2–1 | Renate (3) | Empoli |  |
| 17:00 CEST (UTC+2) |  Merola  17', 79'  | Laporan |  Galuppini  89'  | Stadion: Stadio Carlo Castellani  Penonton: 0 Wasit: Matteo Marchetti  |     |
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| 30 September 2020 | Vicenza (2) | 3–2 (p.w.) | Pro Patria (3) | Vicenza |  |
| 17:00 CEST (UTC+2) |  Giacomelli  45+1'  Marotta  92' (pen.)  Vandeputte  108'  | Laporan |  Parker  32'  Latte Lath  113'  | Stadion: Stadio Romeo Menti  Wasit: Giovanni Ayroldi  |     |
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| 30 September 2020 | Chievo (2) | 1–1 (p.w.) (6–7 a.p.) | Catanzaro (3) | Verona |  |
| 18:00 CEST (UTC+2) |  De Luca  41'  | Laporan |  Martinelli  59'  | Stadion: Stadio Marcantonio Bentegodi  Wasit: Francesco Meraviglia  |  |
|   |   | Adu penalti |  |  |  |
|   |  Palmiero   De Luca   Morsay   Grubac   Mogoș   Rigione   Zuelli   Illanes   |   |   Carlini   Curiale   Bayeye   Martinelli   Pinna   Garufo   Casoli   Verna  |  |  |
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| 30 September 2020 | Lecce (2) | 2–0 | Feralpisalò (3) | Lecce |  |
| 18:00 CEST (UTC+2) |  Henderson  69'  Dubickas  88'  | Laporan |  | Stadion: Stadio Via del Mare  Wasit: Ivan Robilotta  |     |
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| 30 September 2020 | Pordenone (2) | 3–0 | Casarano (4) | Trieste |  |
| 18:00 CEST (UTC+2) |  Rossetti  20'  Butic  35' (pen.)  Secli  76'  | Laporan |  | Stadion: Stadio Nereo Rocco  Wasit: Daniel Amabile  |     |
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| 30 September 2020 | Reggiana (2) | 0–3 (4–3 a.p.) | Monopoli (3) | Reggio Emilia |  |  |
| 18:00 CEST (UTC+2) |  Marchi  85' (pen.), 112' (pen.)  | Laporan |  Starita  60'  Montero  107' (pen.)  | Stadion: Mapei Stadium – Città del Tricolore  Wasit: Antonio Rapuano  |  |  |
|   |   | Adu penalti |  |  |  |  |
|   |  Espeche   Gyamfi   Marchi   Pezzella   Radrezza   |   |   Mercadante   Santoro   Montero   Zambataro   Paolucci  |  |  |  |
 Catatan: Monopoli dianugerahi kemenangan 3-0 karena Reggiana menurunkan pemain yang tidak memenuhi syarat. Pertandingan awalnya berakhir 2–2 setelah perpanjangan waktu dengan Reggiana menang 4–3 melalui adu penalti.
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| 30 September 2020 | Salernitana (2) | 3–0 | Südtirol (3) | Salerno |  |
| 18:00 CEST (UTC+2) |  Tutino  53'  Cicerelli  60'  Capezzi  88'  | Laporan |  | Stadion: Stadio Arechi  Wasit: Daniele Paterna  |     |
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| 30 September 2020 | Venezia (2) | 2–0 | Carrarese (3) | Venice |  |
| 18:00 CEST (UTC+2) |  Johnsen  65', 90'  | Laporan |  | Stadion: Stadio Pier Luigi Penzo  Penonton: 0 Wasit: Riccardo Ros  |     |
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| 30 September 2020 | Brescia (2) | 3–0 | Trapani (3) | Brescia |  |  |
| 20:00 CEST (UTC+2) |  | Laporan |  | Stadion: Stadio Mario Rigamonti  Wasit: Lorenzo Illuzzi  |  |  |
 Catatan: Trapani mengundurkan diri dari pertandingan.
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| 30 September 2020 | SPAL (2) | 0–0 (p.w.) (4–2 a.p.) | Bari (3) | Ferrara |  |
| 21:00 CEST (UTC+2) |  | Laporan |  | Stadion: Stadio Paolo Mazza  Wasit: Simone Sozza  |  |
|   |   | Adu penalti |  |  |  |
|   |  Sa. Esposito   Janković   Floccari   Se. Esposito   Tomović   |   |   Antenucci   Marras   Candellone   Minelli  |  |  |