The winner of the 1998/99 UEFA Cup Winners Cup was Italian Lazio , who defeated Mallorca in the final. The Italians no longer had to defend their title, as from the next season the winners of the national cups got places in the UEFA Cup .
Content
Preliminary Round
| Team # 1 | Amount | Team # 2 | 1st match | 2nd match |
|---|---|---|---|---|
| Rudar | 2-0 | Designer | 2-0 | 0: 0 |
| Vaduz | 0: 5 | Helsingborg | 0: 2 | 0: 3 |
| Lausanne | 7: 2 | Cement (Ararat) | 5: 1 | 2: 1 |
| Cork city | 2: 3 | CSKA (Kiev) | 2: 1 | 0: 2 |
| Ekranas | 4: 5 | Apollo | 1: 2 | 3: 3 |
| Apolonia | 1: 9 | Genk | 1: 5 | 0: 4 |
| Bangor City | 0: 3 | Haka | 0: 2 | 0: 1 |
| Levski | 9: 2 | Locomotive 96 | 8: 1 | 1: 1 |
| Metallurgist (Liepaja) | 4: 3 | Keflavik | 4: 2 | 0: 1 |
| Grevenmacher | 2: 8 | Rapid (Bucharest) | 2: 6 | 0: 2 |
| Lantana | 0: 6 | Heart of Midlothian | 0: 1 | 0: 5 |
| Amika (Wronki) | 5: 0 | Hibernians | 4-0 | 1-0 |
| Gotha | 1:10 | MTK | 1: 3 | 0: 7 |
| Glentoran | 1: 3 | Maccabi (Haifa) | 0: 1 | 1: 2 |
| Wardar | 0: 3 | Spartak (Trnava) | 0: 1 | 0: 2 |
| Copenhagen | 10: 0 | Karabakh (Agdam) | 6: 0 | 4-0 |
| Partisan | 2: 1 | Dynamo (Batumi) | 2-0 | 0: 1 |
1/16 Finals
| Team # 1 | Amount | Team # 2 | 1st match | 2nd match |
|---|---|---|---|---|
| CSKA (Kiev) | 1: 5 | Lokomotiv (Moscow) | 0: 2 | 1: 3 |
| Metallurgist (Liepaja) | 0: 4 | Sporting (Braga) | 0: 0 | 0: 4 |
| Reed | 3-0 | MTK | 2-0 | 1-0 |
| Paris Saint-Germain | 3: 4 | Maccabi (Haifa) | 1: 1 | 2: 3 |
| Panionios | 5: 1 | Haka | 2-0 | 3: 1 |
| Apollo | 3: 3 (pen.) | Jablonec 97 | 2: 1 | 1: 2 (a.d.) |
| Lazio | 3: 3 | Lausanne | 1: 1 | 2: 2 |
| Newcastle United | 2: 2 | Partisan | 2: 1 | 0: 1 |
| Chelsea | 1-0 | Helsingborg | 1-0 | 0: 0 |
| Levski | 1: 6 | Copenhagen | 0: 2 | 1: 4 |
| Rapid (Bucharest) | 2: 2 | Volerenga | 2: 2 | 0: 0 |
| Besiktas | 4: 2 | Spartak (Trnava) | 3-0 | 1: 2 |
| Heerenveen | 4: 1 | Amika (Wronki) | 3: 1 | 1-0 |
| Rudar | 0: 2 | Vartex | 0: 1 | 0: 1 |
| Duisburg | 1: 6 | Genk | 1: 1 | 0: 5 |
| Heart of Midlothian | 1: 2 | Mallorca | 0: 1 | 1: 1 |
1/8 Finals
| Team # 1 | Amount | Team # 2 | 1st match | 2nd match |
|---|---|---|---|---|
| Lokomotiv (Moscow) | 3: 2 | Sporting (Braga) | 3: 1 | 0: 1 |
| Reed | 3: 5 | Maccabi (Haifa) | 2: 1 | 1: 4 |
| Panionios | 4: 2 | Apollo | 3: 2 | 1-0 |
| Lazio | 3: 2 | Partisan | 0: 0 | 3: 2 |
| Chelsea | 2: 1 | Copenhagen | 1: 1 | 1-0 |
| Volerenga | 4: 3 | Besiktas | 1-0 | 3: 3 |
| Heerenveen | 4: 5 | Vartex | 2: 1 | 2: 4 (a.d.) |
| Genk | 1: 1 | Mallorca | 1: 1 | 0: 0 |
Quarter Finals
| Team # 1 | Amount | Team # 2 | 1st match | 2nd match |
|---|---|---|---|---|
| Lokomotiv (Moscow) | 4-0 | Maccabi (Haifa) | 3-0 | 1-0 |
| Panionios | 0: 7 | Lazio | 0: 4 | 0: 3 |
| Chelsea | 6: 2 | Volerenga | 3-0 | 3: 2 |
| Vartex | 1: 3 | Mallorca | 0: 0 | 1: 3 |
Semifinals
| Team # 1 | Amount | Team # 2 | 1st match | 2nd match |
|---|---|---|---|---|
| Lokomotiv (Moscow) | 1: 1 | Lazio | 1: 1 | 0: 0 |
| Chelsea | 1: 2 | Mallorca | 1: 1 | 0: 1 |
Final
| May 19, 1999 |
| Villa Park , Birmingham Spectators: 15,021 Judge: Gunter Benko |