He won the South American Footballer of the Year award in 1987 and 1993, He is the fifth highest assister in the history of national teams and the twelfth overall, including clubs, and in 1999, he was also named one of the top 100 players of the 20th century by World Soccer.

[12] He played a major role during the golden era of Colombian football in the 1990s, representing his national side in three FIFA World Cups and five Copa América tournaments.

In the MLS, Valderrama scored relatively few goals (16) for a midfielder, but is the league's fourth all-time leader in assists (114) after Brad Davis (123), Steve Ralston (135) – a former teammate, and Landon Donovan (145).

[22] Valderrama was a member of the Colombia national football team from 1985 until 1998; he made 111 international appearances, scoring 11 goals, making him the most capped outfield player in the country's history.

[3][6][24] On 5 September 1993, Valderrama contributed to Colombia's historic 5–0 victory over South American rivals Argentina at the Monumental in Buenos Aires, which allowed them to qualify for the 1994 World Cup.

[25] Although much was expected of Valderrama at the World Cup, an injury during a pre-tournament warm-up game put his place in the squad in jeopardy; although he was able to regain match fitness in time for the tournament, Colombia disappointed and suffered a first-round elimination following defeats to Romania and the hosts USA.

[6] A team-player, Valderrama was also known to be an extremely selfless midfielder, who preferred assisting his teammates over going for goal himself;[14][28][29][30] his tactical intelligence, positioning, reading of the game, efficient movement, and versatile range of passing enabled him to find space for himself to distribute and receive the ball, which allowed him both to set the tempo of his team in midfield with short, first time exchanges, or create chances with long lobbed passes or through balls.

[3][9][31][32][33][34][35] Valderrama's most instantly recognisable physical features were his big afro-blonde hairstyle, jewelry, and moustache,[19] but he was best known for his grace and elegance on the ball, as well as his agility, and quick feet as a footballer.

His control, dribbling ability and footwork were similar to those of smaller players, which for a player of Valderrama's size and physical build was fairly uncommon, and he frequently stood out throughout his career for his ability to use his strength, balance, composure, and flamboyant technique to shield the ball from opponents when put under pressure, and retain possession in difficult situations, often with elaborate skills, which made him an extremely popular figure with the fans.

Valderrama's mix of physical strength, two-footed ability, unpredictability and flair enabled him to produce key and incisive performances against top-tier teams, while his world class vision and exceptional passing and crossing ability with his right foot made him one of the best assist providers of his time; his height, physique and elevation also made him effective in the air, and he was also an accurate free kick taker and striker of the ball, despite not being a particularly prolific goalscorer.

[6][7][8] Despite his natural talent and ability as a footballer, Valderrama earned a reputation for having a "languid" playing style, as well as lacking notable pace, being unfit, and for having a poor defensive work-rate on the pitch, in particular, after succumbing to the physical effects of ageing in his later career in the MLS.

In his first season in France, he also initially struggled to adapt to the faster-paced, more physical, and tactically rigorous European brand of football, which saw him play in an unfamiliar position, and gave him less space and time on the ball to dictate attacking passing moves; he was criticised at times for his lack of match fitness and his low defensive contribution, which initially limited his appearances with the club, although he later successfully became a key creative player in his team's starting line-up due to his discipline, skill, and his precise and efficient passing.

"[19] In February 2004, Valderrama ended his 22-year career in a tribute match at the Metropolitan stadium of Barranquilla, with some of the most important football players of South America, such as Diego Maradona, Enzo Francescoli, Iván Zamorano, and José Luis Chilavert.

On 1 November 2007, Valderrama accused a referee of corruption by waving cash in the face of Oscar Julian Ruiz when the official awarded a penalty to América de Cali.