Enrique Iglesias & Anna Kournikova: Photos of the Couple Over the Years

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May 8, 2023 10:00AM EDT
Anna Kournikova, Enrique Iglesias
Bei/Shutterstock

Check out photos of longtime partners Enrique Iglesias and Anna Kournikova over the years!

Enrique Iglesias and Anna Kournikova are going strong! The Spanish singer and the Russian retired tennis player have been together since 2001, and while they still haven’t gotten married, they are madly in love. The couple met on the set of the music video “Escape” and started dating soon after. They welcomed fraternal twins Lucy and Nicholas in 2017 and daughter Mary in 2020. Enrique and Anna give occasional glimpses into their family life on social media, but overall they prefer to keep their kids out of the spotlight.

Do you love Enrique and Anna as a couple? We sure do! Click through the gallery to see more photos of the power pair from over the years.

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Anna Kournikova & Enrique Iglesias With Twins

Anna Kournikova & Enrique Iglesias With Twins
The Grosby Group / BACKGRID

Anna Kournikova and Enrique Iglesias enjoy a rare outing with her adorable baby twins, Lucy Iglesias and Nicholas Iglesias. They went shopping at the Bal Harbour mall in Miami Beach. 

January 14, 2022, 4:38PM
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Enrique Iglesias & Anna Kournikova Enjoy a Tennis Match

Enrique Iglesias & Anna Kournikova Enjoy a Tennis Match
Andrew Gombert/EPA/REX/Shutterst

Enrique Iglesias and Anna Kournikova watch Serena Williams of the USA play against her sister Venus Williams during their Sony Ericsson Open Tennis Match in Key Biscayne, Florida on Apr. 2, 2009. During a break, the pair chatted.

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova Smile During Tennis

Enrique Iglesias & Anna Kournikova Smile During Tennis
Andrew Gombert/EPA/REX/Shutterst

Anna Kournikova flirts with partner Enrique Iglesias as they watch Serena Williams and Venus Williams play at the Sony Ericsson Open Tennis Match in Key Biscayne, Florida in Apr. 2009. The pair were very into the match!

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova Out

Enrique Iglesias & Anna Kournikova Out
MB Pictures/REX/Shutterstock

Enrique Iglesias & Anna Kournikova out and about on a shopping excursion. The pair were seen in LA in April 2005. 

December 19, 2017, 9:19AM
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Enrique Iglesias Kisses Anna Kournikova

Enrique Iglesias Kisses Anna Kournikova
KEVORK DJANSEZIAN/AP/REX/Shutter

Tennis player Anna Kournikova gets a kiss from Latin pop-star Enrique Iglesias seated courtside during Andre Agassi’s first-round match against Alex Bogomlov, Jr., at the Mercedes-Benz Cup, at the Los Angeles Tennis Center in the Westwood district of Los Angeles in 2004. Anna couldn’t help but giggle!

December 19, 2017, 9:19AM
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Enrique Iglesias Plays With Anna Kournikova’s Hair

Enrique Iglesias Plays With Anna Kournikova’s Hair
KEVORK DJANSEZIAN/AP/REX/Shutter

Enrique Iglesias adjusts the hair of tennis player Anna Kournikova as they watch Andre Agassi taking on Alex Bogomlov, Jr., during the first round match of the Mercedes-Benz Cup, at the Los Angeles Tennis Center in the Westwood district of Los Angeles. Enrique was such a doting boyfriend during the match.

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova Share a Tender Moment

Enrique Iglesias & Anna Kournikova Share a Tender Moment
KEVORK DJANSEZIAN/AP/REX/Shutter

Anna Kournikova gets a kiss from Enrique Iglesias seated courtside during Andre Agassi’s first-round match against Alex Bogomlov, Jr., at the Mercedes-Benz Cup, at the Los Angeles Tennis Center in the Westwood district of Los Angeles. Enrique gave his love a smooch on her forehead!

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova at the Mercedes-Benz Cup

Enrique Iglesias & Anna Kournikova at the Mercedes-Benz Cup
KEVORK DJANSEZIAN/AP/REX/Shutter

Tennis player Anna Kournikova, right, gets a kiss from latin pop-star Enrique Iglesias seated courtside during Andre Agassi’s first round match against Alex Bogomlov, Jr., at the Mercedes-Benz Cup, at the Los Angeles Tennis Center in the Westwood district of Los Angeles. The couple looked so cute! 

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova at ‘Once Upon a Time in Mexico’

Enrique Iglesias & Anna Kournikova at ‘Once Upon a Time in Mexico’
Dave Allocca/StarPix/REX/Shutter

Enrique Iglesias & Anna Kournikova on the red carpet of the ‘Once Upon A Time In Mexico’ premiere in 2003. Anna flaunted her abs at the event with her slinky white outfit!

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova Wow the Red Carpet

Enrique Iglesias & Anna Kournikova Wow the Red Carpet
BEI/REX/Shutterstock

Anna Kournikova and Enrique Iglesias turn years at the New York premiere for ‘Once Upon A Time In Mexico.’ The couple looked so young back then!

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova Arrive at a Premiere

Enrique Iglesias & Anna Kournikova Arrive at a Premiere
CHARLES SYKES/REX/Shutterstock

All eyes are on Enrique Iglesias and Anna Kournikova as they arrive for the premiere of ‘Once Upon A Time In Mexico.’ The couple looked very early 2000s with their ensembles at the 2003 event. 

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova at the VMAs

Enrique Iglesias & Anna Kournikova at the VMAs
TINA FINEBERG/AP/REX/Shutterstoc

Enrique Iglesias arrives with tennis star Anna Kournikova for the MTV Video Music Awards at New York’s Radio City Music Hall. The smitten pair were definitely a hot couple on the red carpet. 

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova Strike a Pose

Enrique Iglesias & Anna Kournikova Strike a Pose
MATT BARON/BEI/REX/Shutterstock

Enrique Iglesias and Anna Kournikova pose for the cameras. The couple attended the 2002 MTV Awards at Radio City Music Hall.

December 19, 2017, 9:19AM
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Enrique Iglesias & Anna Kournikova at the 2002 VMAs

Enrique Iglesias & Anna Kournikova at the 2002 VMAs
ERIK C PENDZICH/REX/Shutterstock

Enrique Iglesias and Anna Kournikova attend the MTV Awards in 2002. The pair definitely rocked some early 2000’s threads at the event at Radio City Music Hall.

December 19, 2017, 9:19AM