How to Make Parlay Bets in Massachusetts - A Betting Guide for Parlays

Massachusetts sports betting sites have officially launched. And because parlay bets are the bread and butter of many systems, you'll need to know the ins and outs of how to make a parlay work for you. School is in session. 

Below, we'll cover the details of these wager types. As you get ready to place parlay bets, be sure to consider claiming various Massachusetts sportsbook sign-up promos.

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What is a Parlay in Massachusetts Sports Betting?

A parlay bet is simply two or more bets combined into a single wager where each piece of the bet - commonly known as a "leg"- is dependent on all the others. The winnings from each leg roll into the next one, so each leg has to win or the entire bet is a loss.

They can also be called "multis" or "accumulators", depending on what country you're in, but in the U.S. you're most likely to see them just called parlays.

Are Parlay Bets Legal in Massachusetts?

First things first: The laws around sports gambling have been signed by Gov. Baker, but it's not like he hit a switch and it's all happening now. It will take a little time to get all the ducks in a row, but placing a parlay bet online or with sports betting apps in Massachusetts will be as legal as booing the Yankees.

How Do Parlays Work?

The double-edged sword of parlays may be self-evident, but here it is in black and white: Every leg you add to a parlay increases the potential payout if it hits. But because each leg has to hit, everyone you add is another chance to junk the whole thing.

A parlay bet requires at least two legs, otherwise, it's just a straight bet. Expect the sports betting sites will cap a maximum number of legs at 10 or 12, but BetMGM made news in 2021 for cashing a 15-leg parlay that hit. 

Building Your Parlay Betting Strategy

Like the rest of your betting system, the way you choose to make parlay bets is going to be a personal decision. When you make your first parlay bet, you may try going with the chalk - betting the heavy favorites. This can get you a feel for how putting together a parlay bet adjusts the odds with each leg, and how it changes the final payout. 

One of the most common parlays is called the two-team parlay. That's just taking two teams (usually basketball or football) to cover their spreads, usually at -110 odds. That adds up to +264 odds.

You can also roll together a three-game parlay on the moneylines, and take an underdog to make the odds a little longer and the winnings more enticing. And as you begin to bet with parlays, you'll want to keep your stakes small until you've got a level of comfort with the way you play.

Additionall you can try things such as the Parlay+ from ESPN BET Massachusetts.

Winning a Parlay Bet

So what does it take to win a parlay bet? Every leg you combined when you placed your bet has to hit. Let's take a hypothetical four-leg bet around a handful of pre-season NFL games.

You could take a popular sportsbook's listing, like BetMGM Massachusetts or others, on three favorites and a slight underdog on the moneylines and get the following:

PickLeg Odds
Patriots over Panthers+105
Seahawks over Bears-210
Packers over Saints-160
Texans over Rams-160

That Texans/Rams game starts latest, so if your other three picks hit, you could find yourself staying up late hoping the Texans pull it off. If the Pats, Seahawks, and Packers all win, but the Texans lose, so do you.

Understanding Parlay Odds

Every time you add a leg, the parlay gets harder to win, since more conditions have to be met, and figuring out the odds can be a lot of math.

Having graduated from a public high school in Massachusetts myself, I'm glad that the online sportsbooks will calculate the parlay odds for me. DraftKings Massachusetts, for instance, has a parlay odds calculator that you can play with to your heart's content. It's never a bad idea to run your wager through an odds calculator, and I have to do it - I just don't trust my arithmetic.

Take a look at that pre-season parlay again and we'll see how the parlay's odds come together.

PickLeg OddsTotal Odds
Patriots over Panthers+105+105
Seahawks over Bears-210+202
Packers over Saints-160+391
Texans over Rams-160+699

How Parlay Payouts Work in Massachusetts

Whether you're using Caesars Sportsbook Massachusetts or other sportsbooks, the parlay payout should be easy to determine once you've worked out the betting odds. At that point, the potential payout is calculated like any individual bet: If you're at minus odds, you need to bet that much in dollars to win $100, and if you're at plus odds, you can claim that amount by betting $100 and winning.

Let's go back to those preseason games. If you're cashing winning moneyline bets of $2.50 on each of those games individually (we're starting small, remember), you'd walk away with $16.94. That's your total stake of ten dollars, plus about seven bucks in winnings.

If you'd bet that same stake on a winning parlay, the listed odds of +699 against a $10 stake would give you a much larger payout: $79.91

You can determine your parlay payouts by using our free parlay calculator

Types of Massachusetts Parlay Bets


The moneyline is the simplest bet there is: You pick a side and if the side you pick wins, so do you. Picking the Bruins at -145 over the Rangers is an example of taking the favorite on the moneyline.


Over/Unders, or totals, are most often bets on the combined final score of a contest. You may see a total for a Celtics/Heat game set at 197.5 points at a sportsbook like FanDuel Massachusetts. You're betting on whether you think the score at the end of the game will be higher or lower than the number set.

Point Spreads

A point spread levels the field by allowing you to bet on the margin of victory, with the favorite needing to win by more points than the number set, while the underdog can lose by up to (but not including) that amount. A large margin of football and basketball parlays are built around the point spread. If the Patriots are listed at +7 against the Ravens, they can lose by 6 and still give you a winning bet, while playing the Ravens at -7 would have to win by 8 to make you a winner.


Teaser bets allow you to adjust the totals or the point spreads to your advantage at the expense of a smaller payout. Because it is a specialized form of a parlay bet, all of your picks need to hit or the entire parlay loses, no matter what you call it. You could tease the Patriots (+8 rather than +2) and the Seahawks (+2 instead of -4) on the spread. Because you're more likely to have the bets win, you'll notice the payout isn't nearly as sexy as if you'd just parlayed them straight.


Pleasers are essentially the opposite of teasers - you're moving the point spread against you (and making the bets that much harder to hit) in exchange for much bigger payouts. They're pretty hard to find on legal online sportsbooks, and when you do find them, they're likely only be around the parlay-friendliest markets, basketball and football.

Round Robin

Round Robin parlays are actually a bunch of small parlays played at once. If you were to pick the Celtics, Warriors, and Spurs to cover their spreads in a Round Robin, the book would build three component two-team parlay wagers: Celtics & Warriors, Celtics & Spurs, and Warriors and Spurs. It's another way to play parlays with a gentler landing if things don't exactly go your way. Note that you can also combine futures parlays that could include the Celtics playoff chances, Patriots AFC odds and Bruins Stanley Cup odds. 

Parlay Cards

A parlay card is a list of spreads, totals, or sometimes player prop bets, either on a piece of paper or a sportsbook site where a bettor can quickly assemble a parlay from these fixed odds. You're most likely to find them in retail sportsbooks, like WynnBet Massachusetts which will appear soon in MGM Springfield and Encore Boston Harbor since the sites and apps will oftentimes want to move the betting odds in the time between physical cards being published and the games starting.

Pros and Cons of Parlays

Depending on the source, a parlay bet is the only way to play, or it's a sucker's bet. Here are some things to consider before you bet.


  • ✅ Excitement. If you've won two bets in your three-team parlay, watching how that last leg plays out can be a real thrill.
  • ✅ Payouts. When you manage to win parlay bets, the winnings will greatly outstrip how you would have done if you'd played them as individual bets. 
  • ✅ Promotions. The books want you to play parlays, so you'll frequently find sportsbooks like bonuses like free bets or parlay insurance, which can credit you back your stake if you miss exactly one leg.


  • ❌ Increasingly hard to win. Every time you add a leg, the chance of your wagers winning gets that much smaller, which is a large part of why it's so hard to consistently win.
  • ❌Strategy. It's tough to implement an actual strategy when making your parlay picks.
  • ❌Fixed odds favor the house. With the varying odds in an online sportsbook, you may be able to find daylight in the betting lines that can reduce the house edge. If you're using a parlay card in a retail sportsbook, you can forget about that.

Tips for Parlay Betting in Massachusetts

Start Small

While you're learning the ropes, keep your bets small in both the stake and the size of the parlay itself. The excitement factor is still there even if you know you're not going to get rich overnight on a three-team parlay. You can also consider parlaying futures odds for a huge payout, such as combining the New England Patriots Super Bowl odds with other futures bets. 

Play The Favorites

You want to win, right? Take a heavy favorite as one of your legs while you're just starting out. It'll probably hit, so even if it doesn't do much for your payout, one leg in the books isn't a bad way to begin.

Up The Legs, Not The Stake

As casual bettors begin to get more comfortable with parlays, they'll frequently bet more money on them. Don't do that. If you lengthen the parlay itself rather than pumping up your stake, you won't be out more money should your bets lose.

Learn More About Parlay Bets in Massachusetts

By now you should have an overall view of the higher-risk, higher-reward world of parlay betting. It's an exciting, tempting sports bet that can make your gambling experience that much more entertaining with operators such as Barstool Sportsbook Massachusetts.

Just remember to know your sportsbook's rules, bet small while you get comfortable, and use a parlay as a garnish rather than as a main course.

Massachusetts Parlay Bets FAQ


Brian Dermody relentlessly tests and reviews all the top sports betting apps available in the US to ensure bettors know exactly what they are getting into when they sign up with a new online bookie.

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