Club Career
In 1994, aged 12, Portillo entered Real Madrid's youth system. During seven seasons he was a prolific scorer, netting 150 goals and breaking a record previously held by Raúl. In 2002 he signed his first professional contract, running until 2007 with a release clause of €35 million.
On 6 October 2002, Portillo made his first main squad appearance, starting in a 5–2 home win against Deportivo Alavés, and ending that season with five goals in only 10 games. He also scored a vital last-minute equaliser against Borussia Dortmund in the UEFA Champions League second group stage, a goal which ultimately proved to be crucial in the Merengues' making it into the knockout stages.
In July 2004, Portillo was loaned to Serie A club ACF Fiorentina, but was recalled by new manager Vanderlei Luxemburgo, who arrived midway through 2004–05. However, the same coach deemed him surplus to requirements and another loan ensued, to Belgian League's Club Brugge KV.
At the end of this loan period, Portillo returned to Real, under newly-hired coach Fabio Capello. With new signing Ruud van Nistelrooy adding to already present Raúl, Antonio Cassano and Ronaldo, he was released from contract, and signed a two-year contract with newly promoted Gimnàstic de Tarragona.
After a very successful individual season (11 league goals, although the Catalan side was relegated from La Liga), he replaced, in July 2007, Roberto Soldado at Osasuna, who returned from loan to Real Madrid. During his first two campaigns, he was used irregularly, and only netted three times in the league.
In late December 2009, Portillo – who was only fourth or fifth-choice striker for Osasuna coach José Antonio Camacho – finally moved clubs, signing until the end of 2009–10 plus two more with second division's Hércules CF. After some time to adjust, he finished the season in the starting XI, netting vital goals in the final stretch (namely in the last round, a 2–0 win at Real Unión), as the Alicante club returned to the first division after 13 years.
In 2010–11, Portillo returned to reserve status, after Hércules signed David Trezeguet and Nelson Valdez in the off-season. He only started through injury or suspension to the pair, and only scored twice in official matches, one coming in a 3–1 away win against Real Sociedad on 3 April 2011, with Hércules being immediately relegated back.
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