| Tourney Name: | European Cup Winners' Cup |
| Year: | 1987–88 |
| Dates: | 23 August 1987 – 11 May 1988 |
| Num Teams: | 32 (first round) 33 (qualifying) |
| Champion Other: |  Mechelen |
| Count: | 1 |
| Second Other: | Ajax |
| Matches: | 63 |
| Goals: | 131 |
| Attendance: | 957273 |
| Top Scorer: | Paulinho Cascavel (Sporting CP) 6 goals |
| Prevseason: | 1986–87 |
| Nextseason: | 1988–89 |
The 1987–88 season of the European Cup Winners' Cup finished with a shock victory by Mechelen in the final against defending champions Ajax. This led to their 1988 European Super Cup title in the club's first ever European campaign (1987–89). As the next season's Belgian league victor it defended its title in a semifinal of the 1988–89 European Cup Winners' Cup. Financial problems have been keeping this last Belgian holder of any European cup away from a position to be as successful again.
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Dunajská Streda won 6–1 on aggregate.
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1–1 on aggregate. RoPS won on away goals----Vllaznia won 6–0 on aggregate.----Mechelen won 3–0 on aggregate.----St Mirren won 1–0 on aggregate.----Real Sociedad won 2–0 on aggregate.----Dinamo Minsk won 4–1 on aggregate.----OFI Crete won 3–2 on aggregate.----Atalanta won 3–2 on aggregate.----Kalmar FF won 1–0 on aggregate.----Sporting CP won 6–4 on aggregate.----Marseille won 1–0 on aggregate.----1–1 on aggregate. Hajduk Split won 4–2 on penalties.----Den Haag won 3–2 on aggregate.----Young Boys won 4–3 on aggregate.----Hamburg won 8–0 on aggregate.----Ajax won 6–0 on aggregate.
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Mechelen won 2–0 on aggregate.----Sporting CP won 5–1 on aggregate.----RoPS won 2–0 on aggregate.----2–2 on aggregate. Young Boys won on away goals.----Ajax won 3–0 on aggregate.----1–1 on aggregate. Dinamo Minsk won on away goals.----Atalanta won 2–1 on aggregate.----The match was interrupted in the 10th minute with the score 0–0 due to tear gas being thrown in the stands by Hajduk fans. The resulting commotion was accompanied with the same fans throwing flares onto the pitch followed by a pitch invasion. The match was resumed some 15 minutes later and completed with Hajduk winning 2–0 on the night and Marseille advancing 4–2 on aggregate. At a disciplinary hearing several days later, UEFA voided the match due to the crowd trouble, awarding a 3–0 win to Marseille and banning Hajduk from European competition for two seasons.
Marseille won 7–0 on aggregate.
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Mechelen won 2–1 on aggregate.----Atalanta won 3–1 on aggregate.----Marseille won 4–0 on aggregate.----Ajax won 2–0 on aggregate.
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Mechelen won 4–2 on aggregate.----Ajax won 4–2 on aggregate.
See main article: 1988 European Cup Winners' Cup Final.
The top scorers from the 1987–88 UEFA Cup Winners' Cup are as follows:
| Rank | Name | Team | Goals |
|---|---|---|---|
| 1 |  Paulinho Cascavel | Sporting CP | 6 |
| 2 | Klaus Allofs |  Olympique Marseille | 4 |
| Piet den Boer | KV Mechelen | 4 | |
 Eli Ohana | KV Mechelen | 4 | |
| Jean-Pierre Papin | Olympique Marseille | 4 | |
| Tony Sealy | Sporting CP | 4 | |
| 7 | Remco Boere | Den Haag | 3 |
 Aldo Cantarutti | Atalanta | 3 | |
| Oliviero Garlini | Atalanta | 3 | |
| Bruno Labbadia | Hamburg | 3 | |
| Juraj Majoroš | Dunajská Streda | 3 | |
| Henny Meijer | Ajax | 3 | |
| Dario Zuffi | Young Boys | 3 |