| 1999-12-19 | CagliarivLecceSerie A · Italy | 0–0 | Serie A · Italy |
| 1999-12-11 | LeccevBariSerie A · Italy | 1–0 | Serie A · Italy |
| 1999-12-05 | RomavLecceSerie A · Italy | 3–2 | Serie A · Italy |
| 1999-11-28 | LeccevVeneziaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-11-21 | IntervLecceSerie A · Italy | 6–0 | Serie A · Italy |
| 1999-11-07 | LeccevUdineseSerie A · Italy | 1–0 | Serie A · Italy |
| 1999-10-31 | LeccevPerugiaSerie A · Italy | 0–1 | Serie A · Italy |
| 1999-10-24 | LaziovLecceSerie A · Italy | 4–2 | Serie A · Italy |
| 1999-10-17 | LeccevRegginaSerie A · Italy | 2–1 | Serie A · Italy |
| 1999-10-03 | BolognavLecceSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-09-25 | LeccevJuventusSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-09-19 | PiacenzavLecceSerie A · Italy | 1–1 | Serie A · Italy |
| 1999-09-12 | VeronavLecceSerie A · Italy | 2–0 | Serie A · Italy |
| 1999-08-29 | LeccevMilanSerie A · Italy | 2–2 | Serie A · Italy |
| 1999-06-13 | ChievovLecceSerie B · Italy | 1–2 | Serie B · Italy |
| 1999-06-06 | LeccevPescaraSerie B · Italy | 0–1 | Serie B · Italy |
| 1999-05-30 | RavennavLecceSerie B · Italy | 1–2 | Serie B · Italy |
| 1999-05-23 | LeccevAtalantaSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-05-16 | NapolivLecceSerie B · Italy | 2–2 | Serie B · Italy |
| 1999-05-09 | LeccevCosenzaSerie B · Italy | 2–0 | Serie B · Italy |
| 1999-05-02 | MonzavLecceSerie B · Italy | 1–1 | Serie B · Italy |
| 1999-04-25 | LeccevTernanaSerie B · Italy | 3–2 | Serie B · Italy |
| 1999-04-18 | CesenavLecceSerie B · Italy | 3–1 | Serie B · Italy |
| 1999-04-11 | LeccevLuccheseSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-04-03 | VeronavLecceSerie B · Italy | 5–1 | Serie B · Italy |
| 1999-03-28 | LeccevCremoneseSerie B · Italy | 2–1 | Serie B · Italy |
| 1999-03-14 | BresciavLecceSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-03-06 | LeccevReggianaSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-02-28 | TorinovLecceSerie B · Italy | 3–1 | Serie B · Italy |
| 1999-02-21 | LeccevF. AndriaSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-02-14 | TrevisovLecceSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-02-07 | LeccevGenoaSerie B · Italy | 3–1 | Serie B · Italy |
| 1999-01-31 | RegginavLecceSerie B · Italy | 1–3 | Serie B · Italy |
| 1999-01-24 | LeccevChievoSerie B · Italy | 2–2 | Serie B · Italy |
| 1999-01-17 | PescaravLecceSerie B · Italy | 0–0 | Serie B · Italy |
| 1999-01-10 | LeccevRavennaSerie B · Italy | 1–0 | Serie B · Italy |
| 1999-01-06 | AtalantavLecceSerie B · Italy | 2–1 | Serie B · Italy |