| Season | Round | Opponent | Final score | Goalscorers PEC Zwolle |
|---|
| 1956-57 | - | VV Nicator | 2–2 | Jan Horst, Wim Gerritsen |
| 1957-58 | - | SC Stadskanaal | 0–1 | |
| 1958-59 | - | SV Zwolle | 4–1 | Leo Koopman (3x), Wim Gerritsen |
| - | DOS | 0–1 | |
| 1960-61 | - | Zwolsche Boys | 4–0 | Leo Koopman (3x), Rinus Nijhoving |
| - | Go Ahead Eagles | 5–4 | Leo Koopman (3x), Dirk van der Wetering (2x) |
| - | SC Heerenveen | 0–4 | |
| - | Cambuur Leeuwarden | 1–3 | Dick van Ekeren |
| 1961-62 | - | NEC | 2–0 | Leo Koopman, Jan Brouwer |
| - | Vitesse | 2–4 | Jan Brouwer, Wim Pothoven (o.g.) |
| 1962-63 | R1 | Stormvogels | 3–1 | Gerrit Voges (2x), Hennie van Nee |
| R2 | Excelsior | 0–1 | |
| 1963-64 | R1 | Go Ahead | 1–2 | Wannie Sterken |
| 1964-65 | R1 | ADO | 0–5 | |
| 1965-66 | Group | VV Zwartemeer | 1–0 | Leo Koopman |
| Group | Zwolsche Boys | 2–1 | Gerrit Voges (2x) |
| Group | SC Heracles | 2–2 | Gerrit Voges, Wolfram Arnthof (e.d.) |
| 1967-68 | Group | Zwolsche Boys | 2–1 | Wim van der Gaag (2x) |
| Group | AGOVV | 1–1 | Anton Vučkov |
| Group | Go Ahead | 0–3 | |
| 1968-69 | R1 | Ajax | 0–4 | |
| 1969-70 | R1 | FC Twente | 0–3 | |
| 1970-71 | R1 | Willem II | 0–1 | |
| 1971-72 | R1 | Ajax | 3–8 | Jan Hoogendoorn, Klaas Drost, Fons Stoffels |
| 1972-73 | R1 | Fortuna Sittard | 2–2 (won on penalties) | Fons Stoffels, Herman Heskamp |
| R2 | FC Volendam | 1–0 | Wim Mensink |
| R3 | Feyenoord | 1–3 | Herman Heskamp |
| 1973-74 | R1 | IJsselmeervogels | 3–1 | Jan Rorije, Herman Heskamp, Jan Verheijen |
| R2 | Sparta Rotterdam | 1–2 | Jan Verheijen |
| 1974-75 | R1 | SV Spakenburg | 2–0 | Herman Heskamp (2x) |
| R2 | FC Wageningen | 1–5 | Klaas Drost |
| 1975-76 | R1 | sc Heerenveen | 2–0 | Yuri Banhoffer (2x) |
| R2 | FC Dordrecht | 1–0 | Tjeerd van 't Land |
| R3 | SVV | 2–0 | Ben Hendriks, Jan Veenstra |
| QF | Ajax | 3–0 | Yuri Banhoffer, Klaas Drost, Peter Gerards (p) |
| SF | Roda JC | 0–1 | |
| 1976-77 | R1 | RKC Waalwijk | 3–3 (won on penalties) | Jan Hendriksen, Peter Gerards (p), Yuri Banhoffer |
| R2 | FC Dordrecht | 2–0 | Rinus Israël, Ype Hamming |
| R3 | Telstar | 2–1 | Ronald Hendriks, Tjeerd van 't Land |
| QF | MVV | 1–0 | Niels Sörensen |
| SF | FC Den Haag | 2–1 | Koko Hoekstra, Tjeerd van 't Land |
| RU | FC Twente | 0–3 | |
| 1977-78 | R1 | FC Eindhoven | 1–1 (lost on penalties) | Ben Hendriks |
| 1978-79 | R2 | MVV | 4–1 | Ron Jans (2x), Rinus Israël, Jan Hendriksen |
| R3 | Sparta Rotterdam | 0–3 | |
| 1979-80 | R2 | DOVO | 4–1 | Ron Jans (2x), Tjeerd van 't Land, Jesper Rasmussen |
| R3 | DS'79 | 3–1 | Peter van der Hengst, Carry Steinvoort, Ben Hendriks |
| 1/8 | Feyenoord | 2–5 (0–3 & 2–2) | Peter van der Hengst (2x) |
| 1980-81 | R2 | Sparta Rotterdam | 2–2 (won on penalties) | Peter van der Hengst, Gerard van Moorst |
| R3 | FC Wageningen | 3–0 | Peter van der Hengst (2x), Ron Jans |
| QF | Go Ahead Eagles | 2–3 (1–1 & 1–2) | Koko Hoekstra, Ron Jans |
| 1981-82 | R2 | FC Groningen | 3–2 | John Delamere (2x), Chris Riemens |
| R3 | Feyenoord | 1–0 | Ron Jans |
| QF | AZ'67 | 3–9 (1–6 & 2–3) | Chris Riemens (2x), John van den Wildenberg |
| 1982-83 | R2 | FC Twente | 0–2 | |
| 1983-84 | R1 | TSV LONGA | 4–1 | Johnny Rep (2x), Rini van Roon, Gerrit Visscher |
| R2 | SV Blerick | 1–2 | Cees van Kooten |
| 1984-85 | R1 | VV Nieuw-Lekkerland | 6–4 (3–3 & replay 3–1) | Jan Mulder (2x), Martin Wiggemansen, Harry van den Ham, Ron Willems, Dean Wilkins (p) |
| R2 | Go Ahead Eagles | 1–2 | Jürgen Müller |
| 1985-86 | R1 | VVV-Venlo | 5–0 | Martin Wiggemansen (2x), Wilco van Buuren, Peter van der Hengst, Aziz Doufikar |
| R2 | Kozakken Boys | 2–0 | Foeke Booy, Gerrit Visscher |
| R2 | HFC Haarlem | 0–1 (0–0 & replay 0–1) | |
| 1986-87 | R1 | BVV Barendrecht | 7–0 | Foeke Booy (3x), Aziz Doufikar, Dean Wilkins, Henry Pelleboer, Wilco van Buuren (p) |
| R2 | DS'79 | 2–3 (extra time) | Wilco van Buuren (p), Foeke Booy |
| 1987-88 | R1 | Achilles '29 | 4–1 | Alex Kamstra (2x), Peter van der Waart (2x, 1x p) |
| R2 | FC Den Haag | 0–2 | |
| 1988-89 | R1 | SV Venray | 2–1 | Ed Roos, Peter van der Waart (p) |
| R2 | Ajax | 1–4 | Fred Patrick |
| 1989-90 | R1 | AGOVV | 5–3 | Jos van Eck (2x), Gert-Peter de Gunst, Richard Roelofsen, Ben Kanselaar (o.g.) |
| R2 | Willem II | 0–1 | |
| 1990-91 | R1 | Oranje Nassau | 1–0 (extra time) | Richard Roelofsen |
| R2 | PSV | 2–1 | Eddy Smook |
| 1991-92 | R2 | VV Rheden | 0–2 | |
| 1992-93 | R2 | VV Katwijk | 3–0 | Stef Hendriks (2x), Remco Boere |
| R3 | RKSV DCG | 2–1 | Remco Boere, Martin Reynders |
| R4 | RKC Waalwijk | 4–1 | Martin Reijnders (2x), Henk Buimer, Henk Loonstra |
| QF | Feyenoord | 1–1 (lost on penalties) | Johan Hansma |
| 1993-94 | R2 | FC Emmen | 0–2 | |
| 1994-95 | Group | Go Ahead Eagles | 1–2 | Henri van der Vegt |
| Group | Jong AFC Ajax | 1–2 | Marco Koorman |
| Group | DOVO | 2–1 | Leo Schellevis, Martin Reijnders |
| 1995-96 | Group | FC Twente | 1–5 | Bernard Aryee |
| Group | Sportclub Enschede | 6–1 | Milles Reingoud (3x), Martin Reynders, Arie Smit, Gerald van den Belt |
| Group | STEVO | 4–1 | Arie Smit (3x), Martin Reijnders |
| R2 | TOP Oss | 2–1 | Lucian Ilie, Milles Reingoud |
| R3 | Roda JC | 1–1 (lost on penalties) | Jan Bruin |
| 1996-97 | Group | Vitesse | 1–1 | Jan Bruin |
| Group | DOVO | 2–3 | Harry Sinkgraven, Lucian Ilie |
| Group | GVVV | 3–2 | Martin Reijnders, Lucian Ilie, Alfred Knippenberg |
| R2 | Fortuna Sittard | 2–1 | Sami Ristilä, Harry Sinkgraven |
| 1/8 | FC Volendam | 2–1 | Jan Bruin, Johan Steur (o.g.) |
| QF | Roda JC | 0–5 | |
| 1997-98 | Group | AZ | 0–6 | |
| Group | HFC Haarlem | 3–3 | Jan Bruin (2x), Martin Reijnders |
| Group | HVV Hollandia | 5–2 | Jan Bruin (2x), Claus Boekweg (2x p), Marco Roelofsen |
| Group | AFC '34 | 2–2 | Sami Ristilä, Gerald van den Belt |
| 1998-99 | Group | De Graafschap | 0–3 | |
| Group | ACV | 0–0 | |
| Group | VV Drachten | 13–0 | Dirk-Jan Derksen (7x), Jan Gerver (3x), Ignacio Tuhuteru (2x), Arne Slot |
| R2 | Willem II | 2–0 | Ignacio Tuhuteru, Geoffrey Prommayon (o.g.) |
| 1/8 | Go Ahead Eagles | 5–2 | Dirk-Jan Derksen (2x), Marco Roelofsen, Arne Slot, Patrick Peelen (o.g.) |
| QF | Ajax | 1–2 | Sieme Zijm |
| 1999-2000 | Group | Cambuur Leeuwarden | 0–3 | |
| Group | Achilles 1894 | 5–0 | Dirk-Jan Derksen, Gerald van den Belt, Ignacio Tuhuteru, Marco Roelofsen, Arjan Bosschaart |
| Group | Flevo Boys | 6–0 | Milco Pieren (3x), Arne Slot, Ignacio Tuhuteru, Jan Gerver (o.g.) |
| R1 | Cambuur Leeuwarden | 1–0 | Claus Boekweg (p) |
| R2 | FC Eindhoven | 2–4 | Dirk-Jan Derksen, Stanley MacDonald (o.g.) |
| 2000-01 | Group | Jong FC Utrecht | 3–3 | Arne Slot (2x), Martijn Abbenhues |
| Group | WHC | 9–0 | Martijn Abbenhues (3x), Dominggus Lim-Duan, Arne Slot, Henk van Steeg, Robert Wijnands, Nick Kok, Helmig van Ommen (o.g.) |
| Group | HVV Hollandia | 0–0 | |
| R1 | ADO Den Haag | 3–1 | Richard Roelofsen (2x), Remco Schol |
| R2 | NAC Breda | 3–1 | Arjan Bosschaart (3x) |
| R3 | Heracles Almelo | 5–1 | Arjan Bosschaart (2x), Richard Roelofsen, John den Dunnen, Claus Boekweg (p) |
| QF | FC Twente | 3–4 | John den Dunnen, Martijn Abbenhues, Jeroen Heubach (o.g.) |
| 2001-02 | Group | FC Emmen | 1–3 | Richard Roelofsen |
| Group | SV Urk | 1–0 | John den Dunnen |
| Group | Achilles 1894 | 4–0 | John den Dunnen (2x), Richard Roelofsen, Dominggus Lim-Duan |
| R1 | AGOVV | 3–1 | Arjan Bosschaart, Arne Slot, Bert Zuurman |
| R2 | FC Eindhoven | 6–3 | Henk van Steeg (2x), Bert Zuurman, Robert Wijnands, Súni Olsen, Dragan Thijssens (o.g.) |
| 1/8 | FC Groningen | 0–3 | |
| 2002-03 | Group | SV Spakenburg | 3–0 | Marino Promes, Dominggus Lim-Duan, Morten Karlsen |
| Group | Jong Vitesse | 2–3 | Marco Roelofsen (p), Arjan Bosschaart |
| Group | USV Elinkwijk | 5–0 | Dominggus Lim-Duan (2x), Richard Roelofsen, Marino Promes, Albert van der Haar |
| R1 | Helmond Sport | 1–0 (extra time) | Richard Roelofsen |
| R2 | De Graafschap | 1–4 | Arjan Bosschaart |
| 2003-04 | R1 | VV Noordwijk | 7–1 | Gorgi Hristov (3x, 1x p), Marino Promes (2x), Ivar van Dinteren, Ivan Tsvetkov |
| R2 | FC Den Bosch | 1–2 | Marino Promes |
| 2004-05 | R1 | Ajax (amateurs) | 3–0 | Bert Zuurman, Ruud Berger (p), Arco Jochemsen |
| R2 | ADO Den Haag | 0–3 | |
| 2005-06 | R1 | VV Nijenrodes | 7–0 | Ruud Berger (4x), Tjeerd Korf (2x), Ivar van Dinteren |
| R2 | NAC Breda | 2–4 | Ivar van Dinteren, Tjeerd Korf |
| 2006-07 | R2 | FC Emmen | 0–1 | |
| 2007-08 | R2 | ONS Sneek | 2–2 (won on penalties) | Derk Boerrigter, Marcel de Bruijn |
| R3 | Go Ahead Eagles | 1–0 | Marcel Kleizen |
| 1/8 | NEC | 2–0 | Derk Boerrigter, Bram van Polen |
| QF | Feyenoord | 1–2 | Tozé |
| 2008-09 | R2 | Cambuur Leeuwarden | 3–3 (lost 3–0 on penalties) | Albert van der Haar (p), Erik Bakker, Thiago Grizolli |
| 2009–10 | R2 | Sparta Nijkerk | 2–2 (won 4–2 on penalties) | Bram van Polen (p), Cecilio Lopes |
| R3 | Jong De Graafschap | 0–1 | |
| 2010–11 | R3 | Willem II | 2–2 (won 5–4 on penalties) | Arne Slot, Sjoerd Ars |
| R4 | FC Twente | 1–1 (lost 5–3 on penalties) | Yanic Wildschut |
| 2011–12 | R2 | SC Cambuur | 1–0 | Nassir Maachi |
| R3 | RKC Waalwijk | 0–1 | |
| 2012–13 | R2 | Roda JC Kerkrade | 1–0 (extra time) | Fred Benson |
| R3 | RKC Waalwijk | 4–2 | Youness Mokhtar (2x), Ronnie Reniers, Rochdi Achenteh |
| R4 | Go Ahead Eagles | 3–2 | Fred Benson (2x), Youness Mokhtar |
| QF | Heracles Almelo | 3–2 | Arne Slot, Fred Benson, Jesper Drost |
| SF | PSV | 0–3 | |
| 2013–14 | R2 | Fortuna Sittard | 2–0 | Rochdi Achenteh, Joost Broerse |
| R3 | Wilhelmina '08 | 4–0 | Ryan Thomas, Giovanni Hiwat, Darryl Lachman, Fred Benson |
| R4 | S.B.V. Excelsior | 4–2 | Fred Benson (2x), Giovanni Hiwat, Rochdi Achenteh |
| QF | JVC Cuijk | 5–1 | Denis Mahmudov (2x), Bart van Hintum, Maikel van der Werff, Joris van Gerwen (o.g.) |
| SF | N.E.C. | 2–1 | Jesper Drost, Maikel van der Werff |
| F | AFC Ajax | 5–1 | Ryan Thomas (2x), Guyon Fernandez (2x), Bram van Polen |
| 2014–15 | R2 | FC Oss | 3–2 | Jesper Drost (2x), Tomáš Necid |
| R3 | HHC Hardenberg | 6–1 | Thomas Lam (3x), Athanasios Karagounis, Bart van Hintum, Ben Rienstra |
| R4 | VVV-Venlo | 1–0 | Tomáš Necid |
| QF | SC Cambuur | 3–2 (extra time) | Thomas Lam, Ryan Thomas, Jody Lukoki |
| SF | FC Twente | 1–1 (won 4–2 on penalties) | Wout Brama |
| F | FC Groningen | 0–2 | |
| 2015–16 | R2 | Feyenoord | 0–3 | |
| 2016–17 | R1 | DVS '33 | 4–1 | Nicolai Brock-Madsen (2x), Bram van Polen, Anass Achahbar |
| R2 | VVV-Venlo | 2–1 | Kingsley Ehizibue, Youness Mokhtar |
| R3 | FC Utrecht | 1–2 | Nicolai Brock-Madsen |
| 2017–18 | R1 | VV De Meern | 5–0 | Stefan Nijland, Younes Namli, Piotr Parzyszek, Wouter Marinus, Youness Mokhtar |
| R2 | Kozakken Boys | 3–2 (a.e.t.) | Younes Namli, Philippe Sandler, Erik Bakker |
| R3 | N.E.C. | 2–0 | Youness Mokhtar, Terell Ondaan |
| QF | AZ Alkmaar | 1–4 | Wouter Marinus |
| 2018–19 | R1 | VV Staphorst | 1–0 | Vito van Crooy |
| R2 | De Graafschap | 5–2 | Zian Flemming (4x), Mike van Duinen |
| R3 | AZ Alkmaar | 0–5 | |
| 2019–20 | R1 | HSV Hoek | 3–0 | Lennart Thy (2x), Dennis Johnsen |
| R2 | Fortuna Sittard | 0–3 | |
