In May 2018, amid the widening legalization of sports betting in the United States, DraftKings began to expand into online and retail sportsbooks to leverage its brand awareness and customer base.

[1] In July 2014, it announced the acquisition of rival DraftStreet, owned at the time by IAC, the third largest player in the fantasy sports space.

[7] In November 2014, DraftKings reached a two-year deal to become the official daily fantasy sports service of the National Hockey League.

[14] Also in July 2015, DraftKings announced a round of funding totaling $300 million, led by Fox Sports, along with the Kraft Group, owners of the New England Patriots, and Boston financial giant Wellington Management.

[16] In August 2015, DraftKings announced that it had been granted a license by the Gambling Commission in the United Kingdom to operate pool wagering services and that it planned to open an office in London.

[19] On October 5, 2015, an article in The New York Times indicated that an employee at DraftKings admitted to inadvertently releasing data before the start of week three's NFL football games.

"[21] The following day, New York Attorney General Eric Schneiderman opened an inquiry into DraftKings and FanDuel, asking each site for a range of internal data and details on how they prevent fraud.

[23][24] On May 2, 2016, Lawrence Wasden, the Idaho Attorney General, banned DraftKings and FanDuel from operating in the state, calling them illegal gambling.

[27] On June 19, 2017, the Federal Trade Commission (FTC) announced that it would seek a preliminary injunction to block the proposed merger.

The FTC felt that the proposed transaction would give the combined company 90% of the U.S. DFS market, which is considered to be a monopoly position.

[29] In September 2017, DraftKings and FanDuel each paid $1.3 million to settle with the Massachusetts Attorney General's office over allegations of unfair and deceptive practices by the companies prior to 2016.

[32] Since launching in New Jersey, DraftKings has opened sports betting operations in New York, West Virginia, Indiana, Iowa, New Hampshire, Massachusetts and Mississippi.

[34][35][36] Hindenburg Research later published a report alleging that SBTech, which accounted for around 25% of DraftKing's revenue at the SPAC consummation, has ties to organized crime in Bulgaria and illegal gambling around the world.

[44] In 2021, DraftKings agreed to pay at least $50 million over a three-year period to distribute a sports and pop-culture podcast hosted by Dan Le Batard.

[51] In September 2024, the company was fined $200,000 by the Securities and Exchange Commission (SEC) for violating Regulation Fair Disclosure when the company's PR team shared material, non-public information about revenue growth on CEO Jason Robins's personal LinkedIn and X (formerly Twitter) accounts before its official earnings release.

[53] Jeffrey Wan filed a class action lawsuit against DraftKings in New York federal court, alleging that the company unlawfully shared users' personally identifiable information (PII) with third parties.