At two, she trained under Dick Dutrow, winning her first stakes victories, the Tempted Stakes and the Gardenia Stakes, both Grade III events. She came third in the Grade I Frizette Stakes. At three she was sent to California to be trained by Charlie Whittingham. With Wittingham, who chose her few races carefully, she won four turf stakes in a row. By the end of her third year she'd won five stakes, including a second in the Grade I Yellow Ribbon Stakes and a first in the Grade I Matriarch Stakes, the first of her three Matriarch victories.
Flawlessly raced for five years, from age two to six, each year but her first winning no less than one Grade I race. Her campaigns earned her the North American distaff grass course championships of both 1992 and 1993. In her fifth year she earned her largest purses, but even at six, she took her third Grade I Ramona Handicap.
Throughout her career she won three runnings of the Grade I Matriarch, three runnings of the Ramona Handicap, and two of the Grade 1 Beverly Hills Handicap, in the process defeating the best of her generation: among them champion Hollywood Wildcat and the New Zealand-bred star Let’s Elope.
Flawlessly retired having earned close to two million six hundred thousand dollars, a winning campaigner on both coasts as well as the Midwest. Her 16 victories included 15 stakes races, eleven of them in graded company, and nine of them Grade 1.
Flawlessly died of kidney problems on September 26, 2002 at the age of 14. She was buried at Elmond Farm near Versailles, Kentucky.
Flawlessly was inducted into the Hall of Fame in 2004.