Born in Jundiaí, Brazil, Reginaldo started his career with Brazilian club Campo Grande. The club was associated with football agency Pedrinho VRP, which helped numbers of Brazilian footballers transferred to Italy. Reginaldo began his professional career with Treviso in 2001, and helped the club win promotion from the third-tier Serie C1 league to the top-flight Serie A championship. On 27 August 2005, Serie A club Udinese signed him outright from Treviso, but loaning Reginaldo back to the Veneto club immediately.
Fiorentina
Followed by the relegation at the end of 2005–06 Serie A season, Reginaldo moved to Serie A club ACF Fiorentina from Udinese for €1 million. He played 27 games and scored six goals for Fiorentina during the 2006–07 Serie A season, after which he moved to league rivals Parma F.C., signing a 5-year contract.
Parma
Reginaldo was signed by Parma for €4.5 million fee. He was one of the forward of the team along with Igor Budan, Cristiano Lucarelli and Bernardo Corradi. Reginaldo started most of the game, and Corradi was the second. That season Parma used 4–3–3 or 4–5–1 formation, and Budan was the topscorer of 7 goals. Among the 4 goals were played along with Reginaldo. Parma were relegated at the end of the 2007–08 Serie A season, but Reginaldo stayed with the club for the 2008–09 Serie B season. Having helped Parma win promotion for the 2009–10 Serie A, he moved to Serie A rivals A.C. Siena, signing a contract on 27 June 2009 in a co-ownership deal.
Siena
In June 2009 Siena signed Reginaldo from Parma in a co-ownership deal for €2.5 million fee as well as Francesco Parravicini in a definitive deal for €2.5 million fee, as part of a cashless swap that Daniele Galloppa moved to Parma also in a co-ownership deal for €5 million fee. Reginaldo followed the team relegated to 2010–11 Serie B. Under Antonio Conte, Reginaldo scored 7 goals and won promotion back to Serie A. The co-ownership also terminated in June 2011 as part of Galloppa and Gonçalo Brandão's deal. Parma got the full card of Galloppa for pre-agreed €5 million fee, while Siena got Reginaldo for pre-agreed €2.5M fee as well as Ângelo for €2.5 million fee.
In March 2012, Siena announced that Reginaldo would play on loan to Japanese club JEF United Chiba. The loan agreement was supposed to run until December 2012 but, after 10 games and no goals, he returned on June to Siena.
Reginaldo returned to Brazil in June 2013 on a free transfer. After poor appearances he was released.
Return to Italy
Circa mid-2016 Reginaldo returned to Italy for Serie C club Paganese. He was about to join Serie D club Sambenedettese in January 2016. However, he was blocked by a non-EU players rule of Italian Football Federation, that amateur club can only sign two non-EU players, given an application was submitted on 31 December 2015. He obtained a resident status in Italy in February 2016, making him eligible for a European Union passport. On 31 July 2017, Reginaldo was signed by another Serie C club Trapani on a one-year contract. In January 2018 he joined Serie B club Pro Vercelli. In July 2018, Reginaldo joined Serie C club Monza. On 17 July 2019, he joined Reggina.
