He also reached the third round of both the 2008 Pacific Life Open in Indian Wells, losing to Guillermo Cañas, and the 2008 Sony Ericsson Open in Miami, losing to Mario Ančić.
to Ivan Ljubičić), and the semifinals of the 2006 Mercedes Cup (l. to Nikolay Davydenko) and a first-round loss at the US Open, BCR Open Romania, and the Kingfisher Airlines Tennis Open. In doubles, he made two semifinal appearance in the 2007 Brasil Open partnering compatriot Agustín Calleri, and in the 2007 Mercedes Cup partnering José Acasuso. Monaco started the year with a quarterfinal appearance at the 2007 Heineken Open, losing to compatriot Agustín Calleri.He reached the second round of the 2007 Miami Masters, losing to David Ferrer. Following his good performance against Federer, he went on to compete in the 2007 Hypo Group Tennis International in Pörtschach and won the title against Gaël Monfils.In the 2007 Mercedes Cup in Stuttgart he lost to Rafael Nadal in straight sets in the quarterfinals.He reached the second round of 2005 Internazionali BNL d'Italia and the 2005 Hamburg Masters, losing to Guillermo Cañas and Jiří Novák, respectively.He lost in the first round of the 2005 French Open to Sébastien Grosjean.