Rosecroft quickly became Prince George's County's political and social center, drawing thousands of people there each racing day.

In the 2000s, Cloverleaf attempted to sell Rosecroft multiple times, but due to lawsuits and politics, all the potential buyers became uninterested.

The next year, Penn National Gaming purchased the racetrack with the hope to make it a racino, and Rosecroft reopened in 2011.

Starting in 1990 and ending in 1995, the racetrack hosted the Messenger Stakes, the second leg of the Triple Crown of Harness Racing for Pacers.

In September 1947, a meeting was held about bringing a harness racetrack to Maryland, specifically Prince George's County,[3] and Rosecroft was chosen to be the site.

[13] Each year during the Miller era, several thousand people traveled from across the country to wager on and watch the horses.

[16] Owners, trainers, and drivers from across the United States moved their farms to Maryland in the 1950s following the opening of Rosecroft, hoping to compete with the best horses.

[13] In 1984, the Hambletonian Society created the Breeders Crown, a traveling series of races to showcase the best 2-year-old and 3-year-old horses throughout North American and Canada.

[31] According to The Washington Times writer Rick Snyder, Vogel did not know the horse racing business and made mistakes that negatively affected the industry in Maryland.

The Potomac Stakes was previously held at Freestate Raceway and generated one-million-dollar-plus handles on several occasions.

[36][37] In 1991, two people were interested in buying the track: Fred Weisman, a California businessman, and former National Football League player Mark May.

[40] In 1992, Western Hanover, the richest horse of that year, won two of the three Triple Crown races, including the Messenger Stakes at Rosecroft.

[41] Rosecroft Raceway went into the record books on October 10, 1992, when a three-horse dead heat occurred in the seventh race.

Since Rosecroft had expanded its simulcasting rights,[43] the new grandstand incorporated large-screen televisions and betting windows.

[44] For the 1993 season, Rosecroft's officials decided to stop hosting the five stake races—The Potomac, the Lady Baltimore, The Terrapan, The Turtle Dove, and The North American—inherited when Freestate Raceway closed.

[48][49][50] According to Rosecroft's racing official Allan Levey, Weisman's relatives did not want to operate the track and their only goal was to sell it.

[51] For the 1995 season, Rosecroft could not afford the payment to host five stake races—including the Messenger Stakes—and dropped them from the racing schedule.

They decided to sell both Rosecroft and Ocean Downs to Cloverleaf Enterprises, a horseman's organization, in mid-1995 for $11 million.

[51] Cloverleaf accepted a $10.6 million loan from Bally Entertainment in hopes that a casino would be allowed at Rosecroft.

[56] In 1994, the Delaware General Assembly approved slot machines for the state's three racetracks,[57] and the first racino opened in December 1995.

[58] This helped the horse racing industry in Delaware, as approximately 10 percent of all gross revenue is used to increase the purses.

Maryland passed a casino bill in 2007, but Rosecroft was not one of the locations sanctioned for expanded gambling by the law.

[73] Penn National said it was hoping to convince the state to allow slot machines at the track, even though voters did not approve Prince George's County as a gambling location.

[74] On July 28, 2011, the Maryland Racing Commission agreed to allow Penn National Gaming to secure a $1.4 million line of credit to cover operating losses at Rosecroft for fiscal years 2011 and 2012.

[74] Disputes between tracks and simulcasters about revenues, however, led to a delay in reaching new agreements on broadcast rights.

To resolve a conflict of interest, Penn National sold its financial stake in the Maryland Jockey Club's in July 2011.

[78] Rosecroft owed $1.24 million in unpaid disbursements under its previous simulcast license, and the parties were negotiating about how much of this debt Penn National would pay.

Penn National also announced its intent to spend $1 million in the coming year to renovate the property, which would include razing old horse barns, putting a new roof on the betting parlors, and upgrading the HVAC system.

[86] Before his heavyweight championship tenure, George Foreman beat Sylvester Dullaire at Rosecroft on July 14, 1969.

[99] Each table in the dining room has its own television, which can be used to watch horse racing—either from Rosecroft or other tracks around the world.