In her testimony on Friday, Constand denied ever having intimate contact with Cosby prior to the night in January 2004 that she said he drugged and molested her, but Mesereau showed her a 2005 deposition in which she testified that she told her mother she'd occasionally been affectionate toward him.
Defence lawyers had similarly attacked her credibility in June when the first trial on these charges against Cosby ended in a mistrial after jurors became deadlocked.
Five of his other accusers have testified in this trial.
Defence lawyers for Bill Cosby hammered away at his main accuser's account on Monday, focusing on her cellphone records that they suggested contradicted her story.
"When I was talking to him my anger was so fierce, I had broken capillaries in my eyes and my eyes were like two pools of blood", Constand, who traveled from Ontario, Canada to testify, said of the January 2005 phone call.
The non-disclosure agreement allowed Constand to discuss her accusations when involved in a federal or state investigation, the prosecution said.
Andrea Constand testified Cosby knocked her out with pills and sexually assaulted her at his home in 2004.More news: Facebook responds to how it collects data when you are logged out
She said she was "very combative" with Cosby, demanding he tell her the medication he'd given her daughter and what he'd done to her. His first trial on the charges ended past year in a mistrial after a Pennsylvania jury couldn't come to a unanimous decision. However, she has since modified her statement, saying she "recalls a Margo".
Constand's mother followed her on the witness stand and bolstered her account, testifying about a phone conversation she said she had with the comedian about a year after the alleged assault in which he described in graphic detail their sexual account and then apologized.
In this call, Gianna Constand tried to ask when Cosby would send her the name of the drug he gave to her daughter when she was allegedly assaulted.
"You told police you called him", Mesereau said pointedly.
Ms Constand, who was director of operations for the Temple University women's basketball team at the time, said she was calling only on matters of business at the university, where he was a powerful trustee.
Constand has testified that she saw the former TV star as a mentor and had previously rejected his advances.
Bliss listed several jobs and career opportunities that Gianna Constand was unaware of at NBC and the 2004 Summer Olympics in Athens, Greece, that Andrea Constand interviewed for because of her connection to Cosby.More news: Spotify to announce important changes to its mobile app next week
Agrusa's ability to question Constand about her $3.4 million civil settlement with Cosby was limited due to a ruling from the judge.
Yesterday, under questioning by Mesereau, Constand denied knowing Jackson, rooming with her or ever speaking to her. And she said her phone calls to Cosby were about basketball and had nothing to do with romance. But Constand's phone records show she did not make any calls to Cosby's mansion that month.
In this case, Cosby's defense attorney Tom Mesereau has argued that Constand was a "con artist" who was obsessed with Cosby's money and fame.
O'Neill said he was anxious he'd have to wait to have the procedure during the week, delaying testimony and keeping sequestered jurors in their hotel longer.
Like last time, though, the defence team hit a brick wall when it asked Constand about a key figure in the case, Marguerite Jackson, who says Constand spoke about fabricating sexual-assault allegations against a celebrity to file suit.
The judge has ruled that Jackson can take the stand at the retrial but indicated he could revisit the issue after Constand was finished testifying.More news: New York Yankees vs. Miami Marlins
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