2020 (Vancouver Whitecaps): Montero finished his third season in Vancouver with five goals and five assists in 11 starts and 16 appearances.
2019 (Vancouver Whitecaps): Montero returned to Vancouver for his second stint, scoring eight goals to win his second WFC Domenic Mobilio Golden Boot award, and recording three assists in 22 starts and 32 MLS appearances. He had two game-winning goals, and his three goals off the bench was tied for most in MLS. Montero was named to the MLS Team of the Week following his performance in the Cascadia Cup tilt versus Portland Timbers in Week 11. He finished the year strong scoring an equalizer and a game-winner, and tallying a game-winning assist, all on 90 minutes or later, in three consecutive matches in September. Montero also made one start and appearance in the Canadian Championship.
2018-19 (Sporting CP): Prior to rejoining the ‘Caps in 2019, Montero had a second stint with Portuguese Primeira Liga giants Sporting Clube de Portugal, making 18 starts in 37 appearances, helping Leões hoist the 2017-18 Taça da Liga while scoring nine goals across all competitions, including five in the UEFA Europa League.
2017 (Vancouver Whitecaps): Montero started two of his three CONCACAF Champions League appearances, scoring a goal in his Whitecaps FC debut versus New York Red Bulls on March 2. He went on to win the WFC Domenic Mobilio Golden Boot award after scoring 13 goals in the regular season, matching his career-high for a single season. In addition, he also contributed with six assists, four leading to game-winners. Montero figured in at least two goals, by scoring or assisting, in the same game six times during the season. Highlights from his season include a brace in his first meeting against his former Seattle Sounders FC side, and then scoring a shorthanded equalizer in the midseason rematch. In the MLS Cup Playoffs, he scored one goal, the eventual winner, in the 'Caps first ever postseason victory in the Knockout Round against San Jose Earthquakes. Montero would start all three of the 'Caps playoff matches.
2013-16 (Sporting CP): After four successful seasons in Seattle, Montero moved on loan to Sporting CP in 2013. After scoring 13 goals in 29 appearances during his first year, the move was made permanent. His initial stop in Portugal featured a total of 37 goals and 12 assists in all competitions, including five UEFA Champions League appearances, and three goals and four assists in seven Europa League appearances. Montero also helped Sporting CP win the 2014-15 Taca de Portugal, by equalizing the match in added time, as Leões would go on to win in a shootout.
2013 (Millonarios): Montero would return to play in Colombia in 2013 when he joined Millionarios FC on loan from Seattle Sounders FC in the top tier of Colombian soccer. Montero would score eight goals in 22 appearances with the team.
2009-12 (Seattle): Montero scored 47 goals and provided 34 assists in 119 regular season appearances from 2009 to 2012 with Seattle Sounders FC. He left as the all-time leading goal-scorer in Sounders FC franchise history, scoring a total of 60 goals in all competitions. Included in that tally are seven goals and two assists while helping Seattle win three U.S. Open Cup titles, as well as six goals and four assists in the CONCACAF Champions League. During his previous time in MLS, Montero was named a three-time All-Star and the 2009 Newcomer of the Year.
2005-08 (Deportivo Cali): Montero began his professional career in 2005 with Deportivo Cali in his home country. Among his 22 total goals for Cali, 16 came in 22 matches during the 2008 season when he led the top tier in scoring. He also led the league in scoring with 13 goals in 18 appearances during the 2006 season while on loan at Atlético Huila. INTERNATIONAL
Montero has made four appearances for the Colombian men's national team. He achieved his first international cap on May 9, 2007 in a 4-0 win against Panama. His most recent appearance was August 12, 2009 in a friendly match against Venezuela.
Signed on March 4, 2021.