2008–09 Serie A was the 67th Serie A season in the history of Società Sportiva Calcio Napoli, and their 83rd overall.
The 1999–2000 season was Società Sportiva Lazio's 100th season since the club's existence and their 12th consecutive in the top division of Italian football. In this season, Lazio won their second Scudetto of their history, and their third Coppa Italia, completing an historical double.
S.S.C. Napoli returned to Serie A, following a couple of years in Serie B, where the club had rebuilt itself following the disastrous 1997-98 season, when it scored merely 14 points from 34 games.
Parma Associazione Calcio did not manage to compete for a much-vaunted first Serie A title, which still proved elusive. In the summer following the end of the season, star striker Hernán Crespo ran out of patience, and signed with champions Lazio for a then-world record transfer fee, in a deal that saw Matías Almeyda and Sérgio Conçeicão join Parma. Parma did manage to hold on to Lazio targets Gianluigi Buffon and Lilian Thuram, maintaining hope that the club could break its duck in 2000–01.
The 1999–2000 season was Juventus Football Club's 102nd in existence and 98th consecutive season in the top flight of Italian football.
The 1999–2000 season saw Associazione Sportiva Roma continue its long drought of titles, finishing a frustrating 6th place in Serie A.
Associazione Calcio Fiorentina did not manage to repeat its near-miss season from 1998–99, and instead missed out on qualification to the Champions League, following an inconsistent season. Its topscorer Gabriel Batistuta finally gave up on clinching the Serie A title with Fiorentina, and switched to Roma in the summer, a move which was greeted with controversy since Roma had only finished sixth in the 1999–2000 season.
Associazione Calcio Milan did not repeat its successful season in 1998–99, and fell back to third in Serie A, as well as crashing out of the Champions League, following a lackluster performance in the First Group Phase. In fact, Milan ended up last in the group, and was not even qualifying for the remainder of the UEFA Cup.
Unione Calcio Sampdoria completed its fall from grace by being relegated to Serie B, just eight years after its league title in 1990-91. Similarly to Napoli the year before, the club was no longer a financial power when it came to signing players, and its star player Ariel Ortega did not deliver to the degree Sampdoria had hoped for.
S.S.C. Napoli continued its steady decline with another lacklustre season. Once more, goalscoring was at a premium, with only 28 goals being scored in the 34 league games. Coach Luigi Simoni was sacked and replaced by youth team coach Vincenzo Montefusco, who led the team to the Coppa Italia final against Vicenza, where Napoli won at home thanks to Fabio Pecchia's goal, but lost 3-0 away from home, and therefore failed to win the trophy. The 13th place in the domestic league was the worst for 14 years, and one year on, Napoli was ultimately relegated.
In the 1997–98 season, the Italian football club Inter Milan, managed by Luigi Simoni, won the UEFA Cup and achieved second place in the Serie A league.
Piacenza Calcio did not manage to renew their stay in Serie A, in the club's debut season at the top level of Italian football. The performance from the team was not too poor however, considering it was only a point from the 14th place that would have kept Piacenza up.
Piacenza Calcio managed to secure a penultimate-round survival in their second attempt to establish themselves in Serie A. Much thanks to the presence of 14-times goal scorer Nicola Caccia and creative midfielder Gianpietro Piovani, plus a tight defensive line, Piacenza had five points in hand to the relegated Bari.
Piacenza Calcio once again survived in Serie A, this time being on the brink of relegation, and having to beat Cagliari in Naples in a so-called spareggio to decide which team would stay up. Thanks to a 3-1 victory, Piacenza was able to hang onto their Serie A status, which was all that could be expected from new coach Bortolo Mutti. Despite losing Nicola Caccia to Napoli, Piacenza was able to count on a reliable goal scorer in Pasquale Luiso, who grabbed 14 goals in his debut season in Serie A.
Piacenza Calcio recorded their best ever finish in the top echelon of Italian football, finishing 12th in Serie A, but just two points above the relegation zone. This was in spite of key players Pasquale Luiso (Vicenza) and Eusebio Di Francesco (Roma) leaving the club before the season began.
Piacenza Calcio had their most successful season ever, with 41 points in 34 games, albeit just three points above the relegation zone. Much thanks to 15 times goal scorer Simone Inzaghi, Piacenza was able to secure a fifth consecutive season in the top flight. The remarkable finish with seven wins out of the last eleven, was key in determining the survival.
Piacenza Calcio had the highest-scoring season in the club's history, but in spite of this, a defeat to Verona in the final round would have rendered relegation. Two goals from Dario Hübner helped sealing a 3–0 victory, which propelled Hübner to become top scorer of the entire Serie A, tying for 24 goals with David Trezeguet. The ex-Brescia hitman Hübner came following the promotion, and aged 34, he reached the very top of his level.
