3, 2023: Recent comments by the executive director of the Maine Gambling Control Unit indicate the state remains on track for the launch of sports betting in November. The Department of Public Safety, Gambling Control Unit announces that Maine sports betting will arrive on Friday, Nov. 31, 2023: DraftKings joins Caesars Sportsbook in Maine as it partners with the Passamaquoddy Tribe. 3, 2023: Caesars Sportsbook and DraftKings accept the first legal Maine sports betting wagers online at 9:00 a.m. The following timeline recaps the history of sports wagering in the Pine Tree State: Milton Champion, the executive director of the Maine Gambling Control Unit, has noted that “It’s a matter of when, not if, for Maine sports betting.”