Surfside is a big, imposing bay mare standing 16.3 hands high[2] bred in Kentucky by her owner, William T. Young's Overbrook Farm.
As a descendant of the broodmare Furlough, Flanders was related to several major winners including One Count, Mrs Penny and Hatoof.
Starting the 1.15/1 favorite ahead of the Bob Baffert-trained Miss Wineshine, she was always in contention but sustained her first defeat as she was beaten one and a quarter lengths into second by Circle of Life.
On her three-year-old debut, she started 1/5 favorite for the Grade III Santa Ysabel Stakes on January 9 and won by eight lengths from Rings A Chime, to whom she was conceding eight pounds.
Only three fillies appeared to oppose Surfside in the Grade I Las Virgenes Stakes a month later and she again started at odds of 1/5, despite conceding at least six pounds to her opponents.
On March 12 Surfside faced Spain and Rings A Chime again (at level weight) in the Grade I Santa Anita Oaks and started at odds of 2/5.
She disputed the lead from the start, took the advantage in the straight and held on to win by three-quarters of a length and a nose from Kumari Continent and Classy Cara.
Day sent Surfside to the front from the start and the filly opened up a clear lead on the backstretch and maintained a narrow advantage into the final turn.
Three weeks later, Surfside was matched against colts and older horses in the Grade II Clark Handicap over nine furlongs at Churchill Downs and started second favorite behind the Belmont Stakes runner-up Aptitude.
[Fillies capable of beating colts] should have a head like a princess (which Surfside doesn't have), a butt like a washer woman, and a walk like a hooker.
On February 18 at the same track, Surfside started 2/5 favorite for the Grade I Santa Maria Handicap, but after disputing the early lead she dropped back and finished last of the five runners behind the Argentinian mare Lovellon.
[7] In the Eclipse Awards for 1999, Surfside finished third behind Chilukki and Cash Run in the poll to decide the title of American Champion Two-Year-Old Filly.