| Tournament details | |
|---|---|
| Teams | 28 | 
| Final positions | |
| Champions |  Al Ittihad (1st title) | 
| Runners-up | .svg.png.webp) Chunnam Dragons | 
| Third place | .svg.png.webp) Kashima Antlers | 
| Fourth place | .svg.png.webp) Al Talaba | 
The winners of the 1998–99 Asian Cup Winners' Cup, the association football competition run by the Asian Football Confederation, are listed below.
First round
West Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg | 
|---|---|---|---|---|
| Kazma  | 5–2 |  Al Wahda | 2–0 | 3–2 | 
| Al Ahli  | 0–3 | .svg.png.webp) Al Talaba | 0–0 | 0–3 | 
| PAS  | 10–3 |  Al-Seeb | 10–1 | 0–2 | 
| Al Ahli  | (w/o)1 |  Al Nejmeh | ||
| Khujand  | 2–5 |  Pakhtakor | 1–1 | 1–4 | 
| Nisa Aşgabat .svg.png.webp) | 2–1 |  Kaisar Kzyl-Orda | 1–0 | 1–1 | 
| Al Ittihad Jeddah  | bye | |||
| Al Nasr  | bye | 
1 Al Nejmeh withdrew.
East Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg | 
|---|---|---|---|---|
| Sinthana  | 5–2 |  Woodlands Wellington | 4–1 | 1–1 | 
| Ho Chi Minh City Customs  | 2–5 |  Sarawak | 1–2 | 1–3 | 
| Chunnam Dragons  | (w/o)1 |  Police SC | ||
| Salgaocar  | 1–4 |  Beijing Guoan | 1–0 | 0–4 | 
| Mahendra Police  | 0–2 |  New Radiant | 0–0 | 0–2 | 
| Happy Valley  | (w/o)2 |  PIA | ||
| Yangon City Development .svg.png.webp) | bye3 | |||
| Kashima Antlers  | bye | 
1 Police SC withdrew. 
2 PIA FC withdrew. 
3 Yangon City Development had been drawn against the representatives of Indonesia, where the 1997/98 season was abandoned and the cup cancelled due to political and economic turmoil in the country.
Second round
West Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg | 
|---|---|---|---|---|
| Kazma  | 4–2 |  Al-Nasr | 3–0 | 1–2 | 
| PAS  | 1–2 | .svg.png.webp) Al Talaba | 0–1 | 1–1 | 
| Al Ahli  | 1–7 |  Al Ittihad | 0–0 | 1–7 | 
| Nisa Aşgabat .svg.png.webp) | 5–6 |  Pakhtakor | 5–0 | 0–6 | 
East Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg | 
|---|---|---|---|---|
| Yangon City Development .svg.png.webp) | 0–4 |  Sarawak | 0–1 | 0–31 | 
| New Radiant  | 4–6 |  Happy Valley | 3–1 | 1–5 | 
| Sinthana  | 1–11 |  Kashima Antlers | 1–2 | 0–9 | 
| Beijing Guoan  | 0–4 |  Chunnam Dragons | 0–2 | 0–2 | 
1 Yangon City Development were unable to field a team for the second leg to player illness.
Quarterfinals
West Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg | 
|---|---|---|---|---|
| Kazma  | (w/o)1 | .svg.png.webp) Al Talaba | ||
| Al Ittihad  | 4–0 |  Pakhtakor | 3–0 | 1–0 | 
1 Kazma withdrew.
East Asia
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg | 
|---|---|---|---|---|
| Happy Valley  | 1–7 |  Chunnam Dragons | 0–3 | 1–4 | 
| Sarawak  | 2–14 |  Kashima Antlers | 2–4 | 0–10 | 
Semifinals
| Al Talaba .svg.png.webp) | 1–3 |  Al Ittihad | 
|---|---|---|
| Qahtan Chathir Drain  36' | Mohammed Al Sahafi  20' Dalian Atkinson  25' Ahmed Bahja  90' | 
| Kashima Antlers .svg.png.webp) | 1–4 | .svg.png.webp) Chunnam Dragons | 
|---|---|---|
| Yutaka Akita  12' | Roh Sang-Rae  33', 86' Kim Jong-hyun  48' Lim Kwan-Sik  66' | 
Third place match
Final
| Al Ittihad  | 3–2 (a.e.t.) | .svg.png.webp) Chunnam Dragons | 
|---|---|---|
| Ahmed Bahja  10' (pen.)  105' Mohammed Noor  84' | Roh Sang-Rae  14', 70' | 
Referee: Ali Bujsaim ( United Arab Emirates)
References
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