They had 3 children, Owen, Margaret and Murrough.
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Grace Ní Mháille was married in 1546 to Dónal an Chogaidh Ó Flaithbheartaigh, tánaiste or heir to the Ó Flaithbheartaigh (O'Flaherty) title, which would have been a good political match for the daughter of the Ó Máille chieftain. As Ó Flaithbheartaigh tánaiste, Dónal an Chogaidh had expectations of one day ruling Iar Connacht, the area roughly equivalent to modern Connemara.
She bore three children during her marriage to Dónal an Chogaidh:
Eógan (Owen): The eldest child, known to be kind and forgiving. Sir Richard Bingham tricked him; Owen was murdered as a result, and Bingham and his troops took over his castle.
Méadhbh (Maeve): Said to be much like her mother, she married Ricard Deamhan an Chorráin a Búrc, 'the Devil's Hook', with whom she had several children. Ní Mháille and a Búrc were supposedly very close, more than once saving her from death.
Murchadh (Murrough): Murrough was said to take after his father, for he enjoyed warfare. He often beat his sister Maeve, and refused to listen to his mother because of her gender. Many sources report that he betrayed his family and joined forces with Sir Richard Bingham after the murder of Owen. When O'Malley heard of this she swore she would never speak to Murrough again for the rest of her life, though she would often insult him. After Dónal an Chogaidh's death, O'Malley left Iar Connacht and returned to Ó Mháille territory, taking with her many O'Flaherty followers.
In 1565, Dónal was killed in an ambush while hunting in the hills surrounding Lough Corrib; this was, undoubtedly, part of Dónal's wider struggle with the Joyces for control of Hen's castle on the lough. Gráinne returned to her own lands and established her principal residence on Clare Island. She allegedly took a shipwrecked sailor as her lover. The affair only lasted briefly as he was killed by the MacMahons of Ballyvoy. Seeking vengeance, Gráinne attacked the MacMahon castle of Doona in Blacksod Bay and killed her lover's murderers on Cahir Island. Her attack on Doona Castle earned her the nickname 'Dark Lady of Doona'.
