For Mauresmo, this first-round tie puts her up against a player who was in the headlines this year after posing for Playboy.
Although Harkleroad has failed to garner wide-spread attention for her on court-exploits, the world No74 is, nonetheless, a potentially tricky opponent.
Mauresmo has won 24 career titles, her other Grand Slam victory coming in Australia in 2006, and has already made it clear that the end of her career is fast approaching.
Having suffered the ignominy of a second-round defeat at the French Open last month to 19-year-old Spanish qualifier Carla Suarez Navarro, she appears desperately short of confidence and motivation.
"I want to keep on playing but at the same time I am wondering if it's the right thing to do," said Mauresmo earlier this year.
"It's been like that for the last few months. At some point that leaves you wondering whether it might be best just to pack it all in. But we are not quite there yet - I still want to keep trying."
Having been a fixture in the top 10 of the women's game, Mauresmo finds herself on the road to possible tennis anonymity and her current ranking highlights how far things have slipped. Since the magical high of two Slams in 2006 Mauresmo has failed to get past the fourth round at any Slam event.
In contrast, Venus Williams, the reigning champion, is full of confidence despite not having competed in any warm up grass court tournaments.
She is aiming for a fifth title at the championships and says she wants another of the famous plates for her home.
"The advantage is that you won it last year and it will never be taken away from you," said the seventh seed, who faces Britain's Naomi Cavaday.
"It will always be yours and you can hug the plate at night if it gets cold.
"I just think Wimbledon is the ultimate place to play your best tennis - the most wonderful tournament to win would definitely be here."
