He spent most of his professional career with Club Bolívar, where he scored 125 goals in the Bolivian Primera División and finished as the league's top scorer in the 2014–15 season.
In 2005–06, he played in 33 games and scored eight goals for Real Madrid's Juvenil A and, in March 2007, he made his senior debut for the B side,[2] finishing the season in the Segunda División with that sole substitute appearance as they dropped down a level.
[4] On 11 August 2008 he signed a four-year contract with RCD Mallorca, leaving in the same transfer window as his twin brother – the Balearic Islands club retained 75% of the player's rights.
[5] He made his La Liga debut on 25 September 2008 in a 2–0 home win against CD Numancia, starting[6] in what would be his only league match in the entire campaign.
[14] After finishing the 2016 Apertura as top scorer with 16 goals, including one in the final lost to The Strongest,[15] Callejón left Bolívar in January 2017 for the Saudi Professional League's Ettifaq FC, managed by compatriot Juan Carlos Garrido.