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Albert Celades
Celades, a defensive midfielder, was born in Barcelona, went through the club's academy in the early 1990s, and was a sweeper in Louis Van Gaal's 1997-98 title-winning team.
He wasn't always a regular starter during his four years with the first squad. Despite this, he won two league crowns, two Copas del Rey, the UEFA Cup Winners' Cup, and the UEFA Super Cup, in addition to scoring the winning goal in the Clasico in November 1999.
The following season, he transferred to Madrid, where he won two more league titles and the Champions League as a part-time player.
Celades eventually returned to Madrid as Julen Lopetegui's assistant, however the position was only temporary, as Lopetegui was fired after only a few months.
Robert Prosinecki
The Croatian midfielder spent periods at both Clasico clubs during his journeyman career, and is very definitely the only guy to have played for Barcelona, Real Madrid, and Portsmouth.
After joining Real Madrid in 1991, his debut season was nearly ruined by injuries. He only had three appearances, but one of them was against Barcelona, where he scored a spectacular free-kick.
In the following two years, he was more regularly involved, winning a pair of cups before spending a season on loan with Real Oviedo.
In 1995, Prosinecki moved to Barcelona on a free transfer, but injuries struck again. Under Johan Cruyff and Bobby Robson, he was unable to break into the first team and left after one season to join Sevilla as a regular starter.