In 2014, prior to the start of their spring meet, Churchill Downs announced an increase in parimutuel takeout rates.

As a result of the takeout increase, Churchill Downs ranked number 22 in that year's Horseplayers Association of North America Track Ratings.

Churchill Downs filled a void in Louisville left by the closing of Oakland and Woodlawn, two earlier race courses.

The then-rural location was along Louisville and Nashville Railroad tracks, allowing for easy transport of horses.

[5] The new ownership would soon institute many changes, such as commissioning the famous twin spire grandstand in 1895, shortening the length of the signature race to its modern 1+1⁄4 miles (2.0 km) in 1896, and adorning the winner of the Derby with a garland of roses, a tradition that also began in 1896.

[6] In early 1902, Applegate, who had made his fortune as a bookmaker, turned over the day-to-day operation of the track to Charles F. Grainger, then the mayor of Louisville, in an effort to move Churchill Downs away from being primarily known for gambling.

Churchill Downs prospered and the Kentucky Derby then became the preeminent stakes race for three-year-old thoroughbred horses in North America.

During that early period, a new clubhouse was built in order to promote social interaction and new events such as steeplechases, automobile races and band concerts.

The State Fair was held on the grounds, featuring the odd spectacle of two locomotives being intentionally crashed head-on in the infield.

On June 5, 1907, African American jockey James Lee set a record that has never been beaten when he won the entire six-race card at Churchill Downs.

In 1908, parimutuel betting machines were introduced as gambling began to be less controversial again, and the wagering portion of the track's business became more profitable.

[7] On Wednesday, June 22, 2011, an EF2 tornado hit the Louisville area, striking the stables and chapel at Churchill Downs, at EF1 intensity.

The dirt oval main track, on which the Derby is run, is one mile (1.6 km) in circumference and is 79–80 feet (24.1–24.4 m) wide, with a 120-foot-wide (37 m) section for the starting gate.

In October 2013, Churchill Downs began installing a new, ultra high-definition video board built by Panasonic, which became operational in time for the 2014 Kentucky Derby.