River Plate Maldonado began his footballing career in Uruguay, where he started out in the youth teams of
Montevideo club
River Plate, going on his first team debut in 1999 but first team opportunities were limited and he twice returned to his home country of Venezuela on loan. First he went on loan to
Nacional Táchira, where his father was the manager, for the 2001–2002 season and despite only scoring 8 goals he helped the now defunct club to their only title. The following season Maldonado was on loan at
Mineros de Guayana.
Maracaibo In 2003 Maldonado signed for
Unión Atlético Maracaibo where he stayed for three seasons and scored 22 goals. During his time at the club he played 5 games without scoring in the
2004 Copa Libertadores and scored 3 goals in his 6 appearances in the
2006 Copa Libertadores.
O'Higgins In 2006 Maldonado joined Chilean club
O'Higgins where he scored 21 goals in his 42 appearances.
Atlante Maldonado joined
México Primera División side
Atlante F.C. in July 2007, scoring on his debut in a friendly against Tecamachalco. He made his league debut for Atlante on 4 August 2007 against
Jaguares scoring his side's only goal in a match that finished in a 1–1 draw. His goals for Atlante helped the team win the
Apertura 2007 title, their third title and an historic one in their first season since relocating from
Mexico City to
Cancún, Mexico. Maldonado finished the Apertura 2007 campaign as second top goalscorer with 18 goals. His 18 goals for Atlante and the 8 that he had scored earlier in the year with C.D. O'Higgins earned him the 2007 Golden Boot of the Americas award, sharing the honour with
Martín Palermo of
Boca Juniors. In the
Clausura 2008, Maldonado was again Atlante's top scorer, this time with 7 goals, the reigning champions Atlante were however unable to defend their title, missing out on the playoffs following a 3–2 loss to
C.F. Monterrey. Having won the Apertura 2007 Atlante qualified for the
CONCACAF Champions League 2008–09. Maldonado scored in the knock out stages, helping Atlante to the Final of the competition where they defeated
Cruz Azul 2–0 on aggregate.
Xerez Maldonado was signed for an undisclosed fee by newly promoted Spanish
La Liga club
Xerez C.D. on 25 August 2009 after impressing for Atlante in the
2009 Peace Cup in Málaga, Spain. He made his league debut for Xerez on 30 August 2009 in a 2–0 loss to
RCD Mallorca and left the club on 30 December 2009 to join his former club
Atlante F.C. Chivas Maldonado was signed by
Chivas USA during the summer transfer widow after spending two years with Atlante. He had three goals and one assist in league and Superliga. His contract option was declined after only scoring two goals in 10 appearances in league games.
Atlas Maldonado was transferred on loan to
Club Atlas on 5 December 2011. After long negotiations Maldonado was bought by Atlas on 20 December 2011 but had to give Ricardo Jimenez and Hebert Alferez transfers and some money to Atlante so the transfer could happen. ==International career==