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.

Preliminary round

First leg

Second leg

Dinamo Tirana won 5–3 on aggregate.

First round

First leg

Second leg

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.

Second round

First leg

Second leg

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.

Quarter-finals

Notes

First leg

Second leg

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.

Semi-finals

First leg

Second leg

Sampdoria won 4–2 on aggregate. Anderlecht won 2–0 on aggregate.

Final

Top scorers

The top scorers from the 1989–90 UEFA Cup Winners' Cup are as follows: