Caicedo began his career with
Cortuluá in 2010, scoring 1 goal in 8 appearances. He then transferred to
Deportes Quindio in 2011, staying with them for two seasons. Caicedo had a great season in 2012, scoring 13 league goals, including a hat trick against
Deportes Tolima. However, he missed two trainings without explanation, which made it seem like he was going to leave, and in January 2013, Caicedo signed with
Danubio F.C. of Uruguay. Despite the transfer, he only played a few preseason matches before being released from the club because of problems with
Deportes Quindio. In February 2013, Caicedo signed a 1.5 year deal with
CA Independiente of Argentina. His first two goals for the club came in a 3-1 victory against
San Martín de San Juan. He was loaned out to
Independiente Santa Fe after scoring 2 goals in 14 games. He joined
Atletico Huila in 2014 and had a great season, being second in the top scorers list behind
Germán Cano with 14 goals. Caicedo's performances interested
Independiente Medellín, and they signed him the next year, in 2015. In his first season with the club, he was one of the top scorers, and was part of the squad that finished runner-up
that season. In the next season, he won his first title with the club, the
2016 season. He signed on loan with
New England Revolution of
Major League Soccer in December 2018. The deal included a purchase option for New England at the end of the 2019 MLS season, which they decided not to take because of Caicedo's desire to return to Colombia and his subpar performances. On 27 April 2019, he scored two goals against
Sporting Kansas City in a 4-4 draw. Caicedo rejoined Independiente after his loan expired, but signed with
Deportes Tolima midway through the 2020 season. He scored on his debut on 14 September against
Deportivo Pasto in a 3–1 win. Caicedo scored in the opening match of the
2021 season on 18 January, as well as scoring in the semifinal in the
Copa Colombia on 28 January against Pasto. Caicedo was unavailable as Tolima lost in the final against Caicedo's old club, Independiente. After missing the months of March and April with injury, Caicedo returned on 12 May in the
Copa Sudamericana, with the league season paused in the quarterfinals of the
knockout stage. Caicedo returned to the starting line-up for the knockout stage and scored all three goals for Tolima in the two-legged final against
Millonarios, as they won their third title, 3–2 on aggregate. == Honors ==