Early career Montenegro began his career at Paraguayan club
Tacuary where he made 51 appearances and scored seven goals before joining
Segunda División Uruguay side
Deportivo Maldonado.
West Ham United loan He joined West Ham on 29 August 2011 where he signed a season-long loan contract saying, "I am very excited to come here and play in England, I am hoping to get a chance to show the fans what I can do." Montenegro's first and only appearance for the senior squad was as a 78th-minute substitute on 8 January 2012 in a 1–0
FA Cup third round away defeat to
Sheffield Wednesday. At the end of the season, a new contract was not agreed and he returned to Paraguay.
Tacuary He returned to
Tacuary coming on as a second-half substitute in their match against
Libertad in August 2012. He scored two goals in 17 games in his second spell at the club.
Rubio Ñú and Libertad In 2013, he joined
Paraguayan Primera División side
Rubio Ñú where he scored three goals in 14 games. His form earned him a move to fellow
Paraguayan Primera División side
Club Libertad. During the 2013–14 season he scored nine goals in 36 games.
Nacional Asunción In July 2014, Montenegro signed with
Primera División Paraguaya Club
Nacional Asunción to participate in the semi-final stages of the
2014 Copa Libertadores and the Torneo Clasura of the Paraguayan Championship. Replacing injured forward
Fredy Bareiro, Montenegro was in the starting line-up of the first-leg of Nacional's semi-final
Copa Libertadores fixture against
Defensor Sporting on 22 July. In the 35th minute of the first-half, Montenegro opened the scoring for Nacional, giving them a 1–0 lead, the goal was assisted by
Julián Benítez. The fixture concluded 2–0 in favor of Nacional. Montenegro finished a runner up for
Nacional Asunción in the
Copa Libertadores final after losing out to Argentina's
San Lorenzo 2–1 on aggregate in the two legged final.
Loan to Leeds United On 1 September 2014, Montenegro signed on loan for
Leeds United, the deal includes an option to buy. Montenegro was given the number 26 shirt for the 2014–15 season. On 25 October 2014, Montenegro was named in Leeds' matchday squad for the first time when he was named as a substitute against
Wolverhampton Wanderers. He made his debut in the same match as a 2nd half substitute in a 2–1 loss. The match was the last game for Head Coach Darko Milanič who was relieved of his duties minutes after the game. On 4 January 2015, Montenegro made his first Leeds start when he started Leeds'
FA Cup 1–0 defeat against
Sunderland A.F.C. After scoring an impressive 15 goals in 17 league games during the 2016 Primera Division Paraguaya season for Nacional Asuncion, Montenegro was loaned to Cerro Porteño for the remainder of their
2016 Copa Libertadores campaign. Several days later however, the transfer was declined due to a documentation requirement.
Olimpia Loan to Atlético Goianiense On 3 August 2021,
Atlético Clube Goianiense announced the signing of Montenegro on a season-long loan from
Olimpia. ==International career==