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Reps for the musician and athlete did not immediately return PEOPLE’s request for comment.
Enrique Iglesias and girlfriend Anna Kournikova watch as Venus Williams plays her semifinal match against Serena Williams at the Sony Ericsson Open at the Crandon Park Tennis Center on April 2, 2009 in Key Biscayne, Florida.
In 2006, they sat front and center at the Cleveland Cavaliers vs.
Miami Heat game in Miami, posed for photos at Big Pink restaurant and capped off the year with a date at Mauro’s Cafe in December.
And the next year, Kournikova was photographed goofing around in a bikini with Iglesias while they prepared to board a boat in Miami.
She later sported a simple band while out and about.
The couple's privacy was protected by the fact Anna has been out of the public eye for over a year, prompting ongoing questions about the state of the pair's romance.
Enrique and his sportswoman girlfriend have been together since 2001, but they have rarely been spotted out together and keep their romance well away from prying eyes.
Though they didn’t attend many public events together for the rest of the decade, the duo were photographed going on dinner dates and vacationing in St. The former tennis champ also opened up about hopefully becoming a mother in the future in a 2011 interview with , Iglesias reiterated the duo had no plans to wed.
“I’ve never really thought marriage would make a difference,” he told the outlet.