In April 2002 Delgado lost in the first round of the Mallorca Open to a 15 year old Rafael Nadal in Nadal's first ever ATP match.  Nadal would go on to win 14 grand slams as of the 2014 French Open. He has not won a single title (singles and/or doubles) during his career so far. The right-hander reached his career-high singles ranking of World No. 52 in April 1999. Delgado also nearly qualified for the 2006 Wimbledon Championships, but was defeated in the third, and final, qualifying round by Roko Karanušić. He announced his retirement from tennis in May 2011.