| Tourney Name: | European Cup Winners' Cup |
| Year: | 1989–90 |
| Dates: | 16 August 1989 – 9 May 1990 |
| Num Teams: | 32 (first round) 33 (qualifying) |
| Champion Other: |  Sampdoria |
| Count: | 1 |
| Second Other: |  Anderlecht |
| Matches: | 63 |
| Goals: | 165 |
| Attendance: | 1006432 |
| Top Scorer: | Gianluca Vialli (Sampdoria) 7 goals |
| Prevseason: | 1988–89 |
| Nextseason: | 1990–91 |
The 1989–90 season of the European Cup Winners' Cup was won for the only time by Sampdoria in the final against Anderlecht, 2–0 at Nya Ullevi in Gothenburg, on 9 May 1990. They went on to win 1990–91 Serie A, also being runners-up in the 1991–92 European Cup and in the 1988–89 European Cup Winners' Cup. English clubs were still banned from Europe following the Heysel Stadium disaster, meaning Liverpool missed out on a place, but would have a representative again the following season.
|}
Dinamo Tirana won 5–3 on aggregate.
|}
------------------------------------------------------------
Real Valladolid won 6–0 on aggregate.----Monaco won 4–1 on aggregate.----BFC Dynamo won 4–2 on aggregate.----Borussia Dortmund won 3–1 on aggregate.----Sampdoria won 3–0 on aggregate.----Torpedo Moscow won 6–0 on aggregate.----Grasshopper won 4–3 on aggregate.----Anderlecht won 10–0 on aggregate.----Barcelona won 2–1 on aggregate.----Admira Wacker won 3–1 on aggregate.----Panathinaikos won 6–5 on aggregate.----Dinamo București won 2–1 on aggregate.----Groningen won 3–1 on aggregate.----Djurgården won 5–0 on aggregate.----Ferencváros won 6–2 on aggregate.----6–6 on aggregate; Partizan won on away goals.
|}
----------------------------
Real Valladolid won 4–2 on aggregate.----1–1 on aggregate; Monaco won on away goals.----Sampdoria won 3–1 on aggregate.----Grasshopper won 4–1 on aggregate.----Anderlecht won 3–2 on aggregate.----Admira Wacker won 2–0 on aggregate.----Dinamo București won 8–1 on aggregate.----Partizan won 6–5 on aggregate.
|}Notes
------------
0–0 on aggregate; Monaco won 3–1 on penalties.----Anderlecht won 3–1 on aggregate.----Dinamo București won 4–1 on aggregate.----Sampdoria won 4–1 on aggregate.
|}
----
Sampdoria won 4–2 on aggregate.----Anderlecht won 2–0 on aggregate.
See main article: 1990 European Cup Winners' Cup final.
The top scorers from the 1989–90 UEFA Cup Winners' Cup are as follows:
| Rank | Name | Team | Goals |
|---|---|---|---|
| 1 | Gianluca Vialli | Sampdoria | 7 |
| 2 | Marc Degryse | Anderlecht | 4 |
| Milko Đurovski | Partizan | 4 | |
| Marc Van Der Linden | Anderlecht | 4 | |
 Dorin Mateuţ | Dinamo București | 4 | |
| Luc Nilis | Anderlecht | 4 | |
| Florin Răducioiu | Dinamo București | 4 | |
 Dariusz Dziekanowski | Celtic | 4 | |
| 9 |  Ramón Díaz |  Monaco | 3 |
 Mats Gren | Grasshopper | 3 | |
| Mikael Martinsson | Djurgården | 3 | |
 Gerhard Rodax | Admira Wacker | 3 | |
| Dimitris Saravakos | Panathinaikos | 3 | |
| Yuri Savichev | Torpedo Moscow | 3 | |
 George Weah | Monaco | 3 |