The 1998–99 Coppa Italia was the 52nd edition of the tournament, which began on August 23, 1998, and ended on May 5, 1999. Parma won the 1998–99 Coppa Italia tournament for the 2nd time in club history and first since the 1991–92 competition. Parma defeated Fiorentina in the finals, winning on the away goals rule with an aggregate score of 3–3.
| Tournament details | |
|---|---|
| Country |  Italy |
| Dates | 23 Aug 1998 – 30 May 1999 |
| Teams | 48 |
| Final positions | |
| Champions | Parma (2nd title) |
| Runner-up | Fiorentina |
| Third place | Bologna |
| Tournament statistics | |
| Matches played | 95 |
| Goals scored | 232 (2.44 per match) |
| Top goal scorer(s) | Hernán Crespo (6 goals) |
← 1997–98 | |
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Lucchese (2) | 4–2 | Napoli(2) | 2–2 | 2–0 |
| Alzano Virescit (3) | 2–3 | Torino (2) | 1–1 | 1–2 |
| Ancona (3) | 1–5 | Ravenna(2) | 0–1 | 1–4 |
| Atletico Catania (3) | 0–5 | Brescia (2) | 0–1 | 0–4 |
| Castel di Sangro (3) | 2–1 | Perugia (1) | 1–0 | 1–1 |
| Cesena (2) | 5–2 | Pescara(2) | 2–2 | 3–0 |
| Chievo (2) | (a) 1–1 | Foggia(3) | 0–0 | 1–1 |
| Cosenza (2) | (a) 3–3 | Treviso (2) | 1–1 | 2–2 (aet) |
| Cremonese (2) | 1–4 | Atalanta (2) | 0–2 | 1–2 |
| Gualdo(3) | 2–1 | Fidelis Andria(2) | 1–1 | 1–0 |
| Livorno (3) | 1–4 | Reggina (2) | 1–1 | 0–3 |
| Lumezzane (3) | 3–3 (a) | Cagliari(1) | 3–1 | 0–2 |
| Monza (2) | 0–2 | Lecce (2) | 0–2 | 0–0 |
| Nocerina (3) | 3–4 | Hellas Verona (2) | 2–2 | 1–2 |
| Padova(3) | 3–3 (6–5 p) | Reggiana (2) | 2–1 | 1–2 |
| Ternana (2) | 3–4 | Genoa (2) | 1–1 | 2–3 |
p=after penalty shoot-out
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Torino(2) | 2–3 | Milan(1) | 2–0 | 0–3 |
| Atalanta(2) | 2–1 | Empoli(1) | 2–1 | 0–0 |
| Brescia(2) | 3–5 | Vicenza(1) | 3–2 | 0–3 |
| Cagliari(1) | 1–2 | Venezia(1) | 0–0 | 1–2 |
| Castel di Sangro(3) | 2–0 | Salernitana(1) | 0–0 | 2–0 |
| Chievo(2) | 3–4 | Roma(1) | 2–2 | 1–2 |
| Gualdo(3) | 2–6 | Udinese(1) | 2–2 | 0–4 |
| Internazionale(1) | 1–0 | Cesena(2) | 1–0 | 0–0 |
| Lazio(1) | 4–1 | Cosenza(2) | 2–1 | 2–0 |
| Lecce(2) | (a) 4–4 | Piacenza (1) | 1–2 | 3–2 (aet) |
| Lucchese(2) | 1–2 | Bari(1) | 1–0 | 1–2 |
| Padova(2) | 1–2 | Fiorentina (1) | 1–0 | 0–2 |
| Parma(1) | 4–0 | Genoa(2) | 3–0 | 1–0 |
| Reggina(2) | 1–4 | Bologna(1) | 1–1 | 0–3 |
| Sampdoria(1) | 2–1 | Hellas Verona (2) | 2–0 | 0–1 |
| Ravenna(2) | 0–6 | Juventus(1) | 0–2 | 0–4 |
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Juventus (1) | (a) 3–3 | Venezia (1) | 1–1 | 2–2 (aet) |
| Atalanta (2) | 2–2 (5–4 p) | Roma(1) | 1–1 | 1–1 |
| Bari(1) | 1–2 | Parma(1) | 1–2 | 0–0 |
| Fiorentina(1) | 5–0 | Lecce(2) | 1–0 | 4–0 |
| Internazionale(1) | 2–1 | Castel di Sangro(3) | 1–0 | 1–1 |
| Sampdoria(1) | 1–2 | Bologna(1) | 0–0 | 1–2 |
| Udinese(1) | 1–0 | Vicenza(1) | 1–0 | 0–0 |
| Lazio(1) | 4–2 | Milan(1) | 3–1 | 1–1 |
p=after penalty shoot-out
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Udinese(1) | 3–6 | Parma(1) | 3–2 | 0–4 |
| Atalanta(2) | 3–3 (a) | Fiorentina(1) | 3–2 | 0–1 |
| Lazio(1) | 4–6 | Internazionale(1) | 2–1 | 2–5 |
| Juventus(1) | 2–2 (a) | Bologna(1) | 1–2 | 1–0 |
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Internazionale(1) | 1–4 | Parma(1) | 0–2 | 1–2 |
| Bologna(1) | 2–4 | Fiorentina(1) | 0–2 | 2–2 (aet) |
| Parma | 1–1 | Fiorentina |
|---|---|---|
Crespo  16' |
Batistuta 81' |
Attendance: 21,038
Referee: Domenico Messina
| Fiorentina | 2–2 | Parma |
|---|---|---|
| Řepka 48' Cois 62' |
Crespo 42' Vanoli 71' |
Attendance: 39,070
Referee: Stefano Braschi
3–3 on aggregate. Parma won on away goals rule.
Dates: 27 May 1999, 2nd leg: 30 May 1999
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Internazionale | 2-4 | Bologna | 1-2 | 1-2 |
