Cuadrado is known for his direct, offensive style of play along the right flank, and is capable of both scoring goals himself as well as creating goalscoring opportunities for his teammates. He is capable of playing both as a wide midfielder, or as a winger in an attacking trident, due to his ability to make attacking runs down the wing. He often utilises his speed, flair, and technical skills to beat opponents in one on one situations and create space and time for him to shoot on goal, or deliver crosses to strikers in the area. Due to his playing style, which frequently involves taking on full-backs on the flank, and subsequently running towards the touch-line to deliver balls into the area, he has been labelled one of the few “traditional” wide midfielders in the current game. Tim Vickery, a reporter on South American football, stated that as Colombia’s defensive players played near the goal in order to cover for veteran centre-back Mario Yepes, Cuadrado’s pace, agility, creativity and dribbling ability on the right wing moved the team forward at the 2014 World Cup. Vickery also added that, in addition to his main role on the wing, Cuadrado is also adept as an attacking right back or wing back, due to his energy and work-rate. A versatile player, he is also capable of playing on the left, a position which allows him to cut into the middle and shoot on goal with his stronger, right foot. In his early career, he was initially deployed as central or defensive midfielder, and he has also been deployed as a forward, as an attacking midfielder, or as a second striker on occasion.