Oaklawn Park opened on February 24, 1905. During the early years the track only ran six races a day.
The first Arkansas Derby was run in 1936 for a purse of $5,000. In 1941 purses again hit a record for the largest purses in Oaklawn history. By 1943, the Arkansas Derby had a purse of $10,000. Unlike most American tracks Oaklawn stayed open in 1944 but the Second World War closed Oaklawn Park in 1945. After the end of the war the track hit unprecedented levels of prosperity. This financed a major clubhouse renovation and a resurfacing of the track. Throughout the 1950’s the track continued to climb in handle, attendance and money. In 1961, the track extended the season to 43 days.

In 1965, the Arkansas Derby was a $50,000 stakes race. The Arkansas Derby became a $100,000 stakes in 1972 and the following the year the Fantasy Stakes, a prep race to the Kentucky Oaks, was first run. The Racing Festival of the South was created in 1974. The festival is a week with one stakes race everyday leading up to the Arkansas Derby. In 1975 a major renovation was completed which included a five-level, glass-enclosed addition to the north end of the grandstand, near the top of the stretch. The addition included a general admission area, 400 extra box seats and 2,500 reserved seats, a kitchen, a dining room and a private club.

In 1983, the all time record handle was established. The track reached a goal of averaging $3 million in wagering every day. For the 56-day season, the handle amounted to $168,740,923. That same year the purse for the Arkansas Derby was increased to $250,000. In 1984, the purse was again lifted this time to $500,000. In 1985 things went the other way as betting declined 8.1% and attendance 3.7% as compared to 1984. In 1990 the track was forced to race on Sundays to recoup some of the lost revenue.