Born in
Buenos Aires, Montenegro began his professional career at
Club Atlético Huracán in 1997. He subsequently signed for
Club Atlético Independiente, going on to represent the club on three different spells and teaming up with sibling
Ariel in the first. In the 1999 January
transfer window, Montenegro moved to France with
Olympique de Marseille, being loaned several times by the
Ligue 1 side for the duration of his contract, mostly to teams in Spain (
Real Zaragoza – where he contributed four matches to their
conquest of the
Copa del Rey – and
CA Osasuna, both in
La Liga). He then played in quick succession for Independiente and
Club Atlético River Plate, before spending parts of two seasons in the
Russian Premier League with
FC Saturn Ramenskoye. Montenegro returned to his main club for the
2006–07 season, going on to often act as
captain and scoring in double digits in three of his first four years, including a career-best 15 goals in
2008–09. He moved abroad again in 2009, signing with
Mexico's
Club América for
$3.5 million after lengthy negotiations. He made his
Liga MX debut for his new team on 2 August, in a 1–2 home loss to
Monarcas Morelia. Late in the same month, he scored from his own half in a 7–2 rout of
Deportivo Toluca F.C. also at the
Estadio Azteca. On 22 December 2012,
free agent Montenegro rejoined Independiente for a fourth spell, agreeing to a one-and-a-half-year contract. In early 2015, he was ousted from the squad after a run-in with manager
Jorge Almirón and forced to train alone. Aged 36, Montenegro returned to Huracán after 13 years having rejected an offer from
Nueva Chicago. He remained on
the bench for
the final of the
Supercopa Argentina, won against
Club Atlético River Plate shortly after his arrival. At the end of the
2017–18 campaign, in which he helped the
Parque Patricios-based side
qualify to the
Copa Libertadores after a fourth-place league finish, Montenegro announced his retirement. ==International career==