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.

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.

[52] 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.