From Serena Williams to Monica Seles: All you need to know about Donald Trump's connection to tennis

From playing with Serena Williams to Former US President Donald Trump has had a longstanding connection with tennis. The Presidential candidate has also attended several editions of the US Open at times.

During 1989, Trump dated Gabriela Sabatini, who went on to win the US Open singles title in 1990 and is now regarded as one of the finest and popular tennis players of her time.

1991 was a year when the politician was linked to a controversy, as there were reports of Monica Seles staying at his Mar-A-Lago estate shortly after withdrawing from that year's Wimbledon Championships due to an injury. This was a time when she won the Australian and French Opens and was the World No. 1 ahead of the grass-court Major.

In 2015, Donald Trump inaugurated a tennis center at the Trump National Golf Club alongside Serena Williams. He also played a little with the then-33-year-old, who served the first point and won it. The politician, however, won the second point.

Donald Trump attended several editions of the US Open, one of them coming in 1988. During that tournament, he was invited to Jimmy Connors' box to watch his quarterfinal against Andre Agassi. Agassi was dominating the match and Trump later shifted to his box to watch the remainder of the fixture.

Connors wrote about this in his book "The Outsider", stating:

"At the 1988 Open, even Donald Trump couldn’t get a ticket to sit in one of the boxes, so Gerry Goldberg invited him into mine to watch my quarterfinal against Agassi."

"After the second set, it was pretty clear who was going to win. Trump got up, left, and reappeared seconds later in Agassi’s box. I guess he knew where the cameras would be," he added.

Another edition of the US Open that Donald Trump attended was in 2015, two years before he was elected President of the United States.

Donald Trump was booed at the 2015 US Open

Donald Trump meets John McEnroe (in cap) at US Open 2015

Trump watched the quarterfinal between Venus Williams and Serena Williams at the 2015 US Open, and was actually booed by the crowd at the Arthur Ashe Stadium when he entered. He hasn't attended the US Open since.

The match turned out to be a thrilling encounter, as Serena Williams beat her sister 6-2, 1-6, 6-3 to reach the semifinals, where she lost to eventual runner-up Roberta Vinci. This put paid to Williams' hopes of winning the Calendar Slam.

In the tennis fraternity Andy Roddick has both often voiced their criticism of Trump on social media. The latter most recently dismissed the Presidential Candidate's claim that government authorities were nabbing young males in the country without parental consent, stating:

"Didn’t ever happen. Because it’s insane."

Anoter tennis great who has often slammed Trump and his statements on social media is 18-time Grand Slam singles champion Martina Navratilova.