The future royal is believed to have met Prince Harry for the first time at Soho House in London just three days before her trip to Wimbledon.
She then found herself in the awkward position of sitting inches away from Prince Harry’s former fling on Centre Court.
It is not clear whether Meghan and Cressida spoke at Wimbledon, but they were both photographed at the exclusive Ralph Lauren event.
The Duchess of Cambridge’s younger sister Pippa Middleton was also spotted sitting within touching distance from the future royal.
Meghan was in attendance to support her close friend Serena Williams take on Russian tennis player Svetlana Kuznetsova, while Pippa was there to watch friend and Swiss champion Roger Federer.
The Suits star had recently returned from a hen party in Greece, and was invited to attend Wimbledon in her role as an ambassador for Ralph Lauren.
She was spotted talking to fashion PR specialist Violet von Westenholtz and stylist Olivia Buckingham in the VIP lounge, where Cressida was photographed.
Ms Von Westenholtz is rumoured to be the individual who initially set up Prince Harry and Meghan on their blind date in July 2016.
Both however refused to reveal the identity of the female friend in their first joint TV interview following their engagement.
Commenting on their first meeting, Meghan said she “didn’t know much” about Prince Harry before they met.
She said: “The only thing I had asked her when she said she wanted to set us up, was ‘is he nice?’
“If he wasn’t kind, it didn’t seem like it would make sense.”
Prince Harry also admitted he had never watched her hit TV show Suits, but said that they fell in love “so incredibly quickly”.
Also in attendance at the match was American Vogue Editor Anna Wintour, who is a steadfast tennis fan and regular fixture on Wimbledon Centre Court.
The Duke of Kent and Princess Michael of Kent were also spotted among the crowds on Centre Court that afternoon.
Meghan and Prince Harry are set to marry on March 19 at King’s George’s Chapel in Windsor Castle.