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Delaware's relationship with parlay wagering didn't begin in 2018 — it began nearly a decade earlier, when the Delaware Lottery quietly started accepting parlay cards on NFL games in 2009. That makes Delaware the longest-running example of state-sanctioned parlay betting in the country, and understanding that history gives you useful context whether you're placing your first multi-leg ticket or just trying to figure out which states are ahead of the curve. If you're still getting up to speed on the mechanics, start with Parlay Betting Basics: How a Parlay Wager Works before diving into the legal timeline below.
How did Delaware become the first state to offer parlay betting?
PASPA — the Professional and Amateur Sports Protection Act — blocked most states from authorizing sports wagering, but Delaware had a partial carve-out tied to its pre-existing lottery structure. Using that opening, the Delaware Lottery launched a limited parlay program in 2009, letting bettors combine NFL game picks on a single ticket through lottery retailers. The offering was narrow compared to today's full-service sportsbooks: no live betting, no props, no same-game parlays. But it was real, state-supervised parlay action at a time when almost nowhere else in the US could say the same.
The broader landscape changed on May 14, 2018, when the Supreme Court struck down PASPA in Murphy v. NCAA, freeing every state to legalize sports betting on its own terms. Delaware moved fast — it fully legalized sports betting in July 2018, just two months after the ruling, building on the infrastructure it had already spent nine years developing. That head start meant Delaware's sportsbook rollout was smoother than most states that were starting completely from scratch.
Why does this history matter for bettors today?
Delaware proved that a state lottery framework could run regulated parlay betting without major scandals or structural failures, which gave other state legislators a concrete data point to cite when pushing for legalization after 2018. By the end of 2024, 38 states plus Washington, D.C., offered some form of legalized sports betting, with approximately 32 permitting statewide online or mobile wagering as of mid-2026. None of that growth happened in a vacuum — early adopters like Delaware showed the regulatory model was workable.
Not every state has followed the same path, though. Mississippi, for example, permits retail sports betting only; online sports betting — including online parlays — is not legal there, which matters if you're traveling or relocating. Some tribes in New Mexico, North Dakota, Washington, and Wisconsin offer sports betting under existing Class III gaming compacts without full state legislation, creating a patchwork where availability depends on which county you're in. Before you open an account anywhere, check Legal States for Online Parlay Betting: Where You Can Place a Ticket to confirm what's actually available where you live.
What should a new bettor understand about parlays before placing one?
Delaware's 2009 parlay cards only offered NFL combinations, but modern sportsbooks let you chain together legs across multiple sports on the same ticket. The core rule has never changed: every leg must win, or the whole ticket loses. That compounding risk is also why payouts scale so dramatically — two legs at −110 each return roughly +265 American odds, meaning a $100 bet nets about $264 in profit, but the house edge compounds with every leg you add. For a clear breakdown of how the math works and what you're actually signing up for, read What Is a Parlay Bet? Plain-English Definition with Examples.
If you're weighing whether a parlay is even the right structure for a given situation, the more useful comparison is usually parlay versus a straight bet on each game individually. Delaware's original lottery parlays didn't give bettors that choice — you picked the card format and that was it. Today you have full flexibility, and exercising it wisely starts with understanding the trade-offs covered in Parlay vs Straight Bet: Which Should You Place?. Legality and bonus availability vary by state; always confirm your jurisdiction's current rules before signing up for any sportsbook. 21+ only. Gambling problem? Call 1-800-GAMBLER.