2003: Two-year-old season

Ashado won in her first start on June 18, 2003, at Belmont Park by seven lengths over a sloppy track. For her next start, she was entered in the Schuylerville Stakes on July 23 at Saratoga and won by three lengths.^[1][4] On August 29, she stepped up in class to the Grade I Spinaway Stakes at Saratoga, where she was the third betting choice in a field of six. She raced off the pace for the first part of the race, then pulled away in the stretch to win by 1+1⁄2 lengths. "My biggest concern was that this filly is so lazy in the mornings that I didn't do enough with her", said Pletcher. "She had three works and they were all slow since the Schuylerville. Fortunately, she is one of those horses that know the difference between the morning and the afternoon."^[5]

Ashado next entered the Frizette Stakes at Belmont Park as the favorite but finished third behind Society Selection.^[1] She then finished second in the Breeders' Cup Juvenile Fillies, held that year at Santa Anita Park. "We were right behind Halfbridled and around the quarter-pole I came up along side her and I thought I had a chance", said jockey John Velazquez. "But that filly, she just had a bit more today. My filly has a future."^[6]

Ashado finished the season with a win in the Demoiselle Stakes at Aqueduct on November 29. After racing off the pace early, she hit the lead in mid-stretch but slowed down and was nearly beaten by late closing La Reina. Pletcher again noted her laziness during morning workouts and said, "She gets a little idle when she makes the lead."^[7] The victory brought her record for 2003 to four wins from six starts, including three Grade I races in which she had a first, a second and a third-place finish (in the Spinaway, Juvenile Filles and Frizette respectively).^[8]

2004: Three-year-old season

Ashado started her three-year-old campaign in March with a win in the Fair Grounds Oaks, then finished second in the Ashland Stakes at Keeneland in April to Madcap Escapade.^[1] For the Kentucky Oaks at Churchill Downs on April 30, Ashado was the betting favorite in a competitive field of 11. On a muddy track, she raced in second behind Madcap Escapade, who opened up a large lead while setting a "blazing" pace for the first six furlongs. Ashado then started closing ground and finally pulled ahead in the final furlong to win by 1+1⁄4 lengths.^[9]

On June 26, Ashado finished second in the Mother Goose Stakes to Stellar Jayne, then faced her again in the Coaching Club American Oaks on July 24. In the Oaks, Ashado handled a muddy track well and defeated Stellar Jayne by 4+1⁄4 lengths. "I put her in good position and let her do her own thing", said Velazquez. "She started going to the lead and waiting, so I spanked her a couple of times to keep her mind interested. She did everything pretty easy."^[10]

In the Alabama Stakes on August 21, Ashado finished third, beaten by Society Selection, who had beaten her a year earlier in the Frizette, and Stellar Jayne. "We were close to the pace, as we anticipated we would be. They were running along, but it concerned me the way the track was changing throughout the day", said Pletcher. "It was becoming a little bit of a tiring track... She prompted some pretty fast fractions, and she got a little tired."^[11] Ashado then won the Cotillion Handicap at Parx Racing as a final prep for the Breeders' Cup Distaff.^[12]

The Breeders' Cup was held that year at Lone Star Park in Texas on October 30. In the Distaff, Ashado got a "perfect trip" and won by 1+1⁄4 lengths over Storm Flag Flying. It was the first Breeders' Cup win for Pletcher, who said, ""Without a doubt, this filly has delivered every start of her life."^[12] She was the first filly since the Breeders' Cup was created (in 1984) to win both the Distaff and Kentucky Oaks, making her the consensus choice for American Champion Three-Year-Old Filly.^[13]

2005: Four-year-old season

Ashado was given a rest then returned to the racetrack in the Grade I Apple Blossom Handicap at Oaklawn Park on April 9, 2005. She raced just off the pace but did not respond when asked in the stretch drive. Instead she finished fifth, her first time out of the money.^[14] Pletcher later blamed himself for not having trained her sufficiently for the race. Ashado then finished second in the Pimlico Breeders' Cup Distaff Handicap in May, where she struggled with "the wrong type of track" according to Pletcher.^[15]

Ashado returned to form in the Ogden Phipps Handicap at Belmont on June 18, winning by an "authoritative" three lengths.^[16] She followed up in the Go For Wand Handicap at Saratoga on August 1 against four other fillies and mares. She hit the lead turning into the stretch then seemed to hesitate. "I said, 'No, Mommy, you're going to have to stay busy; these are the big girls,'" said Velazquez, who then tapped Ashado with the whip three times. Ashado responded by pulling away for an "effortless" victory by 9+1⁄2 lengths.^[15]

Ashado was then upset in the Personal Ensign Stakes at Saratoga in late August, this time by Shadow Cast. "She never seemed to fire", said Pletcher. "She was never dragging Johnny along the way she normally does. She left there flat and ran flat the whole way."^[17] She rebounded in the Beldame Stakes at Belmont, moving to the lead turning into the stretch and then holding off a late charge from Happy Ticket to win by half a length.^[18]

In the final start of her career, Ashado finished third in the Breeders' Cup Distaff, held that year at Belmont Park on October 29. If she had finished first or second, she would have retired as the all-time female money leader. As it was, Pleasant Home pulled off a 30–1 upset when she won by 9+1⁄4 lengths, with Society Selection edging Ashado by a neck for second place. "I would have liked to send her out with a win", said Pletcher, "but you could never be disappointed with the career that this filly has had. It's been a tremendous run these last three years."^[19]

Despite the loss, Ashado still won three Grade I races at age four (the Ogden Phipps, Go For Wand and Beldame), the same number she had earned at three (the Kentucky Oaks, Coaching Club American Oaks and Distaff). She earned the Eclipse Award for Champion Older Female of 2005 with 203 of 257 first place votes, making her the first filly to earn titles at three and four since Life's Magic in 1984–5.^[20]

Ashado was elected to the National Museum of Racing and Hall of Fame in 2014.^[21]