2003 saw Calado contest pan-European series for the first time, driving a Gillard Parilla kart for the PDB Racing Team in the ICA Junior class.

He finished runner-up to Nicholas Risitano in the European Championship, beating future Formula One drivers Sébastien Buemi and Jaime Alguersuari.

He moved up to the ICA class in 2005, and won the European Championship ahead of his future team-mate Jean-Éric Vergne, and also finished runner-up to Armando Parente in the Italian Open Masters.

Sixth in the Italian Open Masters, Calado went to Macau for the International Kart Grand Prix, where he finished as runner-up to Michael Christensen.

He lost a podium finish at Barcelona due to a puncture with two laps remaining,[6] which could have ultimately turned into a win after the post-race disqualification of winner Albert Costa.

Calado moved up to the GP3 Series for 2011, driving for the Lotus ART team alongside Pedro Nunes, Richie Stanaway and Valtteri Bottas.

In a successful season for ART, Bottas won the championship whilst Calado backed him up with second in the drivers' standings, taking a single win at Valencia and five further podium finishes.

After taking pole positions for the Spanish rounds at Catalunya and Valencia, but not being able to convert them into victories, he won his second race of the season at Hockenheim.

At this stage of the championship, he was third in the drivers' standings, but a poor run in the final four races—after crashing in practice at Monza and suffering from food poisoning in Singapore saw him overhauled by team-mate Gutiérrez and compatriot Max Chilton.

Nevertheless, his fifth place in the championship meant that he finished the season as the series' most successful rookie driver, ahead of Felipe Nasr in tenth position.

A consistent season saw him claim two sprint race wins and another five podiums meant he finished third in the standings on 157 points but quite a distance behind the top two Fabio Leimer and Sam Bird.

[10] As a result of this, and his good GP2 form, Force India announced that they had selected Calado as their third driver for the Italian Grand Prix on 2 September 2013, and that he would run in the first practice session.

In 2019 he won the 24 Hours of Le Mans together with Pier Guidi and Daniel Serra behind the wheel of the #51 AF Corse Ferrari 488 GTE Evo.

[14] With a third place at Spa, where Calado overtook Frédéric Makowiecki on the final lap, and a victory at the 24 Hours of Le Mans — Ferrari's first in 50 years — the #51 crew finished fourth in the standings, being beaten to third by the sister car.