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After the 2000–01 season finished in relegation for Reggina, he was shifted to Atalanta as a replacement of Ivan Pelizzoli. In the summer of 2005, he went on loan to Torino, serving as first-choice goalkeeper; the move became permanent in 2006, with Taibi however becoming the backup goalkeeper behind Christian Abbiati. He made his seasonal debut on 13 January 2007. In the 2007–08 season, he joined Ascoli, as Torino acquired the services of Matteo Sereni. Taibi played 47 matches, before he announced his retirement from football in 2009.

In January 2000, Taibi joined Reggina on loan until the end of the season, where he played regularly. After the loan spell ended, Manchester United made it clear that – although Taibi was available for transfer – another loan deal was out of the question, rejecting a bid from Napoli. In July 2000, Manchester United agreed to allow Taibi to rejoin Reggina for a fee of £2.5 million. On 1 April 2001, Taibi scored a goal with a header off a corner kick in the 87th minute against Udinese to equalise the score final score to a 1–1 draw at home. With the goal, Taibi was the second goalkeeper to score from open play in Serie A history after Michelangelo Rampulla in 1992.

In 1999, Manchester United purchased Taibi for £4.5 million, requiring a new goalkeeper after Peter Schmeichel had left for Sporting Lisbon after winning the treble and injuries to both their 1st and 2nd choice goalkeepers: Mark Bosnich and Raimond van der Gouw respectively. He made his debut against Liverpool, where he flapped at a free kick, allowing Sami Hyypiä to score. However, he later made a number of saves, including a one-on-one save from Vladimír Šmicer. United went on to win 3–2 with Taibi getting the Man of the Match award. Taibi competed with the other two goalkeepers, Mark Bosnich and Raimond van der Gouw, for the first-team place, but lost out after a gaffe against Southampton in September 1999 that resulted in Matthew Le Tissier scoring a goal, for which he became synonymous. This match led to Taibi being dubbed 'The Blind Venetian' by one newspaper. He only played four matches, one of them a 5–0 defeat at Chelsea, United's first league defeat since losing to Middlesbrough in December 1998.

Piacenza thought his time was over, so they sold him to the club which had not played him, Milan. This time, Milan played him in half of the 1997–98 season's games as a backup to teammate Sebastiano Rossi. Then Milan sold him to Venezia in 1998. In his first season with Venezia, he played in nearly every game.

Taibi started his career for Licata until 1989. He appeared only once, before moving to Trentino, where he was a first-choice goalkeeper, playing 23 matches. After one season, he moved to Milan in Serie A for the 1990–91 season. As in his first club, he was not used at all, and shortly moved to Como, where he played the following season. After that he moved to Piacenza. Taibi stayed there for five seasons, until the 1996–97 season, and appeared for most of the club's games.

Massimo Taibi (Italian pronunciation: [ˈmassimo taˈibi] ; born 18 February 1970) is a former Italian footballer, who played as a goalkeeper for several clubs, mostly in Italy's Serie A, B, and C1. He had a brief spell at English club Manchester United.