Reilly was born in Anchorage, Alaska.[3] She was paralyzed from the waist down at birth as she was delivered six weeks premature. Her early life was marked by frequent operations, including surgery around 1997 when she had eight spinal discs and two ribs removed.[3]
Reilly began to move towards road events thereafter, particularly the marathon. She was runner-up in the wheelchair section of the Los Angeles Marathon in 2005 and returned to following year to win the race.[1] She became a regular performer at the Boston Marathon, coming fourth in 2005, improving to third in 2006, then taking fifth in 2007.[4][5] She came fourth in the wheelchair race at the Peachtree 10K in 2008.[6] In her second Paralympic appearance, she competed in the 1500 metres, 5000 metres and the marathon (finishing seventh in the latter event).[1] The following year she was runner-up at the Gasparilla Distance Classic, and third at both the 2009 Boston Marathon and Grandma's Marathon. She debuted in the New York City Marathon in November and took seventh place.[2]
She came in fourth at the 2010 Boston Marathon with a time of 1:57:23 hours and set a personal best of 1:41:01 hours at the 2011 race, finishing as runner-up behind Wakako Tsuchida. Reilly represented her country at the 2011 IPC Athletics World Championships. She defeated Tsuchida at the 2012 Boston Marathon, beating her at the line by a margin of one second to win the Boston Marathon title and set a best of 1:37:36 hours.[7] Later that month she took part in the London Marathon for the first time and came in fourth after Canada's Diane Roy.[8]