While neither was physically in court, their attorneys faced off in a New York court on Wednesday about the 15-year-old, who has been living in the UK with his father since December.
The couple, who filed for divorce back in 2008, were reprimanded by a judge in Manhattan for dragging their son through an acrimonious legal battle.
Judge Deborah Kaplan expressed her disappointment in the celebrity parents’ decision to turn to the legal system to help resolve the matter, noting that Rocco had stated he wanted to come to an arrangement "in the most private way possible."
She urged the pair to "take this tremendous pressure off their son" and resolve the dispute swiftly. A second hearing, behind closed doors, will be held in London on Thursday.
"Frankly, both parties here have chosen to live their lives in a very public way, and may welcome the exposure, but the child has not," she said.
"I urge them to consider what is the best interest of their son - which may be to remove him from the spotlight."
The situation between this once united family has since taken a turn for the worse.
The pop diva’s lawyer took aim at the 57-year-old’s ex, claiming Guy “taught his son that court orders and signed statements do not matter."
Hitting back, the director’s lawyer expressed a teenager could not be forced to return to New York.
"Rocco is of an age where he cannot be physically forced to board a plane to come back," he said. "To make such an order is not the way a child should be forced to live."
The upsetting family situation has resulted in Rocco hiring his own lawyer, Ellen Sigal.
"Having this order over his head is stressful and upsetting to him," she explained about her teenage client, who is currently enrolled at a London school.
In December Judge Deborah Kaplan ordered that Rocco should talk with Madonna, and then revisit the issue of which parent he prefers. He has since stayed in the UK with his father and stepmum, Jacqui Ainsley.
In a bid to win her son over, Madonna has taken to social media to express her love for him with a serious of sentimental posts.
The singer published a picture of Rocco on Instagram last week in an angelic, sunlit pose with the caption: "I miss this boy so full of life so full of .." Referring to his star sign, she added: "I hope we see that Leo Sun soon. The light is blinding."
Last month she posted a photo of Rocco as a baby, with the caption written in French which read: "I miss you."
Clearly affected by the critics weighing in on her family drama, Madonna also shared another snap of her other kids, where she lashed out about the struggles of being a working single mother.
“It’s possible to be an entertainer and a good mother!!! Too bad we don’t live in a society where many encourage strong independent single working mums! The next great frontier!”
Madonna and Guy were married for eight years. Alongside Rocco, the pair are parents to their adopted son, David Banda, 10.
Madonna, who is nearing the end of her world tour, has two other children, Lourdes Leon, 19, and ten-year-old Mercy James, who was adopted from Malawi.