When the Seventh Doctor lands on December 30, 1999 in San Francisco, he is gunned down by a gang on the streets of Chinatown. Unaware of his alien physiology, Grace accidentally kills him when she attempts to operate. He subsequently regenerates into his eighth incarnation, and involves Grace in his fight to prevent the Master from opening the Eye of Harmony and destroying the Earth at the stroke of midnight on New Year's Day, 2000. At the end, the Doctor offers to take Grace along with him in the TARDIS, but Grace declines, preferring to stay behind and apply the lessons she has learned from him.
Grace is described by the Doctor as "tired of life but afraid of dying." She is a warm and compassionate person who was disillusioned early in life when she realized that she could not hold back death. As a result, she puts on a cold, aloof front in an effort to protect herself from her feelings and to mask her own insecurity. She realizes this over the course of her adventure with the Doctor and learns to feel hope again, placing it in the form of the Doctor, an alien who can literally come back to life, as well as regaining confidence in herself as a medical practitioner and as a person. She also rapidly develops a romantic attachment to the Doctor, stating at one point, "I finally meet the right guy and he's from another planet."
Grace appears in the Doctor Who comic strip story The Fallen, published in Doctor Who Magazine #273-#276, where she conducts experiments to merge human and Time Lord DNA, the latter obtained from tissue left behind by the Master. However, the Master is not in his Time Lord body, but that of a shape-shifting creature known as a morphant. The resulting hybrid begins to consume people, but is stopped with the Eighth Doctor's help. Grace promises the Doctor she will destroy all the remaining morphant DNA samples, and the two part ways once more. She subsequently appears as a dream image in The Glorious Dead (DWM #287-#296) and makes a one-panel cameo in the last regular Eighth Doctor comic strip adventure, The Flood (DWM #353). In Prisoners of Time, a series to celebrate the 50th anniversary, the Doctor meets her soon after the events of the TV Movie. She travels with him for a while but is overwhelmed by what she sees. Before the Doctor can return her to Earth, she is kidnapped by Adam Mitchell, who is travelling through time to kidnap the Doctor's companions.
In the novelization of the Sarah Jane Adventures episode Death of the Doctor, Sarah Jane lists the current whereabouts of several of the Doctor's former companions, including a "Doctor Holloway" who is looking into new breakthroughs in surgery in San Francisco.
Legal issues
Originally, Grace Holloway was to appear in the second Eighth Doctor novel, Vampire Science, but legal issues with the BBC and Universal prevented this from happening. According to Big Finish, their audioplays cannot use TV-movie characters Grace Holloway or Chang Lee due to Universal's ownership of the characters. Grace's appearance in the comics appears to have been separately negotiated.