Pezzolano comes from the capital city of Montevideo and is a graduate of the local team C.A. Rentistas, were for the senior team he was involved in the age of 18. His team was relegated to the Second Division after a poor season in 2001. He spent the next two years, after which he returned with his team to the First División.
In 2006, he spent in the BrazilianAtlético Paranaense, but after 6 months, he returned to his native country, signing an agreement with Defensor Sporting. In the 2006–07 season he took a decisive role with his team to get the 3rd place in the league and to get to the quarter-finals of the 2007 Copa Libertadores.
In July 2007, Pezzolano signed with Uruguayan giant C.A. Peñarol. But six months later he joined Liverpool Montevideo, scoring a hat-trick in his debut against Central Español.[1] In his first season (Clausura 2008) with the team, he was the top scorer of the tournament, scoring 12 goals in 14 meetings. A year later came up with Liverpool FC in the Copa Sudamericana, but they fall in 1/16 finals.
In August 2009, Pezzolano went on loan to Spanish team R.C.D. Mallorca.[2] He made his La Liga debut on September 19, 2009 meeting with the 4-0 win against Tenerife.[3] Overall, in the 2009–2010 season he played 12 matches in Mallorca, but only one in the starting composition, a team led by Gregorio Manzano took 5th place in the league table.
In July 2012, he returned to his home city to play for the second time in his career with Liverpool Montevideo. In his match return, he scored a penalty goal against Universitario playing the Copa Sudamericana.[7]
In February 2016, he joined CA Torque on a free transfer. He spent a season with them before announcing his retirement on 23 November 2016, aged 33.[8]
Immediately after retiring, Pezzolano became the manager of Torque for the upcoming season.[8] He led the club to the 2017 Segunda División title before leaving the club on 25 November 2017.[9]
On 18 December 2017, Pezzolano was named manager of another club he represented as a player, Liverpool Montevideo.[10] He departed the club on 25 November 2019,[11] after accepting an offer from a foreign club.
Hours after leaving Liverpool, Pezzolano was named in charge of Liga MX side Pachuca, replacing Martín Palermo.[12] He led Pachuca to the play-offs during the 2020–21 season, losing in the semifinals of the 2021 Torneo Guardianes.
On 8 November 2021, after a 15th place finish in the 2021 Apertura tournament, Pezzolano left the club on a mutual agreement.[13]
On 3 January 2022, Pezzolano was announced as new head coach of Brazilian Série B side Cruzeiro, becoming their first head coach after the team's sale to Ronaldo.[14] He reached the finals of the 2022 Campeonato Mineiro.
Pezzolano led Cruzeiro to a promotion to the Série A, and became the champion of the category with the most numbers of anticipated rounds.[15] On 19 March 2023, however, he left the club on a mutual agreement,[16] after their elimination in the 2023 Mineiro.
