| 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.
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Dinamo Tirana won 5–3 on aggregate.
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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.
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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.
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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.
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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:
