2018: two-year-old season Fairyland was ridden by
Ryan Moore when she made her racecourse debut in a six
furlong maiden race at
Naas Racecourse on 7 May and started at odds of
3/1 in a ten-runner field. She raced close to the leaders from the start, took the advantage a furlong from the finish and won "comfortably" by one and three quarter
lengths. Nineteen days later the filly was stepped up in class and matched against male opposition in the
Listed Marble Hill Stakes over the same distance at the
Curragh in which she was partnered by
Seamie Heffernan. After tracking the front-runners she took the lead in the last quarter mile and drew away to win by two and a half lengths and a neck from her stablemates Van Beethoven and Land Force. The second and third placed horses went on to win the
Railway Stakes and the
Richmond Stakes respectively. Heffernan was again in the saddle when the filly was sent to England to contest the
Albany Stakes at
Royal Ascot and started the 5/2 second favourite against seventeen opponents. Racing on the far side of the straight course (the right-hand side from the jockeys' view) she finished a close third behind Main Edition and La Pelosa, both of whom raced on the opposite side of the track. In the aftermath of the race she was reported to be "under the weather" as many of the Ballydoyle horses were affected by a viral infection. After a break of two months, Fairyland returned for the Lowther Stakes at
York Racecourse and started 6/4 favourite ahead of the
Princess Margaret Stakes winner Angel's Hideaway. Ridden by Moore she led for most of the way and after being headed by The Mackem Bullet inside the furlong she rallied in the final strides to regain the advantage and win by a nose. After the race O'Brien said "I'm delighted with her. She did get headed so it was great to see her battle back... She's a lovely filly and [the Cheveley Park Stakes] is the way we'll be heading... she's a big, rangy filly – she looks more like a three-year-old than a two-year-old". Aidan O'Brien commented "We thought she would come forward from York and she did. She's a lovely, big filly and has loads of speed. Donnacha gave her a peach of a ride. We always thought she would maybe get a mile but she's not short of speed and has a lovely mind. We probably wouldn't run her again this season".
2019: three-year-old season On her three-year-old debut Fairyland was ridden by
Frankie Dettori when she was one of fifteen fillies to contest the
1000 Guineas over the Rowley Mile at Newmarket on 5 May. Starting the 15/2 fifth choice in the betting she raced in mid-division before keeping well under pressure to finish fifth behind
Hermosa, Lady Kaya, Qabala and Angel's Hideaway. In the
Irish 1,000 Guineas at the Curragh she never looked likely to win and came home sixth behind Hermosa, beaten more than eight lengths by the winner. Fairyland was dropped back to sprint distances for the
King's Stand Stakes over five furlongs at Royal Ascot and finished fifth behind
Blue Point,
Battaash, Soldier's Call and
Mabs Cross. On her next race she contested the six-furlong
July Cup at Newmarket in which she ran third to the colts
Ten Sovereigns and
Advertise. In the
Nunthorpe Stakes at York of 23 August Fairyland failed to recover from a poor start and trailed home tenth of the eleven runners in a race won by Battaash. The filly maintained her busy schedule in the
Haydock Sprint Cup on 7 September when she ran sixth to
Hello Youmzain beaten just over three lengths by the winner. Eight days after her defeat at Haydock Fairyland was partnered by Ryan Moore when she started at odds for 12/1 for the Group 1 Flying Five Stakes at the Curragh. Soffia (
Sapphire Stakes) started favourite while the other seven runners included Mabs Cross, Soldier's Call, Houtzen (
P J Bell Stakes), Invincible Army (
Duke of York Stakes) and So Perfect (
Lacken Stakes). After settling just behind the leaders Fairyland overtook the front-running outsider Caspian Prince approaching the final furlong and kept on well to hold off the late challenge of her stablemate So Perfect to win by a short head. O'Brien commented "Her best run of the year was back at five at Ascot in the King's Stand. The ground was too soft for her at Haydock and she got upset in the stalls and banged her head before that at York. You would have to be delighted." Fairyland ran in France for the first time on 6 October when she contested the
Prix de l'Abbaye over 1000 metres on
very soft ground at
Longchamp Racecourse but never looked likely to win and came home tenth behind
Glass Slippers. ==Pedigree==