Ranking My Live Betting Experience At Massachusetts Sportsbook Apps

Written By Chris Gerlacher on March 29, 2023Last Updated on April 18, 2023
Ranking the six Massachusetts sports betting apps live betting, from play-ma.com

Six Massachusetts mobile sports betting apps launched about a week before March Madness began.

And all those brands are competing to win over bettors interested in the fastest-growing sports gambling market: live betting.

To see which is best, I placed live March Madness bets on all six of the sports betting apps available in Massachusetts during the initial mobile launch. Here was my experience.

Live betting in Massachusetts

When live betting in Massachusetts, bettors have several platforms to choose from. In my experience, DraftKings and FanDuel had the best live betting experiences. They were followed by Barstool Sportsbook, BetMGM, Caesars Sportsbook and WynnBET.

Here are my rankings:

  1. DraftKings Sportsbook
  2. FanDuel
  3. Barstool Sportsbook
  4. BetMGM
  5. Caesars Sportsbook
  6. WynnBET

In total, I bet $60 across the six books and ended up at a $5.62 loss. It’s proof that I’m no professional sports bettor, but I don’t feel any great need to submit a reimbursement request, either.

This experience showed me why DraftKings and FanDuel are the most popular legal sportsbook apps in the US. Their live odds updates and game trackers are strong, and they got basic functionality right.

The bet slips worked properly, and the live betting sections weren’t glitchy mid-bet. These proved to be the most important differentiators between the leading sportsbook brands and the others.

DraftKings Massachusetts live betting

DraftKings Massachusetts was the only sportsbook on this list that I already had money in. I turned a $5 bonus bet into an $18.50 win on the Chiefs after the Eagles scored a touchdown and the line overreacted.

This time around, I thought I’d try again with a $10 college basketball bet on Baylor against University of California-Santa Barbara. After the game started, I watched the moneyline odds move from around -320 to -305. This was still early in the game when neither Baylor nor Santa Barbara had pulled ahead, and I didn’t want to wait too long for the odds to drift into the -350s or -400s.

The game tracker was only slightly behind the broadcast. It was far enough that DraftKings could react to customers’ cash movements, but close enough that I could’ve watched the game tracker in the car and been pretty much informed.

I got slightly better odds, but I wasn’t particularly brave. I only came out $3.27 ahead.

FanDuel Massachusetts live betting

FanDuel Massachusetts was my first experience depositing at the sportsbook. Having interviewed payment providers, I knew that sportsbook deposits and withdrawals were clunky and, for many bettors, the worst part of the betting process.

I can see why. I tried depositing $10 with Apple Pay, and it didn’t work. I switched to a bank transfer and logged into my bank account from the app. After supposedly depositing my $10, I was left hanging on the processing screen. I exited the screen thinking that I would have to try again.

Instead, the deposit went through, but it was $100 instead of $10. FanDuel’s default deposit is $100, and that may be one of the reasons it’s the most profitable book brand among the Massachusetts sportsbook apps.

Still thinking that only 10 of those dollars were mine, I placed a $10 bet on Marquette when it played Vermont. The moneyline odds opened around -600 and waffled back and forth between -580 and -620. By the time Marquette pulled ahead, I panicked and bet at -620.

Once again, I was not brave, but I came out an extra $1.61 ahead.

FanDuel seemed to have the smoothest game tracker. The animations weren’t jerky, and I didn’t have to wait very long for my live bet to be processed.

Overall, aside from a janky deposit, FanDuel doesn’t have any functional issues. After betting at the other four books, I missed that seamlessness.

BetMGM Massachusetts live betting

Live betting on the BetMGM Massachusetts app was OK. My $10 Apple Pay deposit was successful this time, so I had high hopes for this book.

When I tried to place my bet for the Notre Dame-Utah women’s game, I saw glitches that I didn’t know to look for on DraftKings and FanDuel.

The odds updated like normal, but the gap between Notre Dame and Utah grew so much that moneyline betting became unavailable. The whole line briefly became unavailable while BetMGM was recalculating.

So, I tried my luck on betting the Under 129.5, which seemed like a stretch when only one team was any good. The odds moved from -140 to -120, so I placed my bet.

Then things got weird. When I placed my $10 bet, the app accepted my bet, then the bet slip showed the odds had changed from -120 to -105. That was strange since I thought I’d locked in at -120.

After reloading the screen, it turned out that I had locked into -120. The odds just continued to track live changes from the wrong screen. I began to see why DraftKings and FanDuel have most of the market share in their states.

I was also beginning to learn I was terrible at over/under betting. The final score was 86-52 for a total of 138 points. Under 129.5 wasn’t even close.

Barstool Sportsbook live betting

Barstool Sportsbook Massachusetts didn’t give me any major issues. Once again, I turned to a women’s college basketball games, and once again, the odds between the two teams were so large that moneyline betting was out of the question. Ohio State was always going to beat James Madison.

This time, I tried one of the alternative point total wagers. The Under 140.5 was about 30 cents better than Under 144 or 145. I almost locked in at +140, but the odds moved, and I ended up at +135.

I had no major issues, but Barstool Sportsbook is notorious for limiting its winning customers’ accounts:

Barstool Sportsbook is an otherwise competitive product that’s undermined by these negative customer experiences.

The final score was 80-66, a total score of 146. I was closer than my BetMGM wager, but I was also put off on over/under betting.

At this point, both my winning and lucky streaks were over.

Caesars Sportsbook & WynnBET live betting

Caesars Sportsbook and WynnBET both gave me trouble.

I had to upload my driver’s license to both sites to verify my identity. Normally, that’s not an issue. It’s a common measure for sportsbooks that can’t verify their customers’ identities. My driver’s license address is from Texas, my current address is in Denver, and I’ve moved apartments since creating both accounts.

The shock came when I found out how long it took. I uploaded my driver’s license and utility bill to WynnBET, and my driver’s license to Caesars on Saturday morning. WynnBET confirmed my identity Tuesday afternoon. I reached out to Caesars on Friday and was asked to submit a utility bill, too.

Buyer beware: It’s OK to have to verify your identity, but reach out to the customer support team directly instead of waiting on a book to verify you.

Once I was finally able to make deposits, I placed my last two bets.

Caesars Sportsbook

The Caesars Sportsbook Massachusetts mobile app is not great for live betting. I watched Gonzaga lose to UConn at a brewery with some friends and had an amber ale. The odds on Gonzaga opened at about +145, and I pounced when the odds moved to +165.

After I confirmed my odds and placed my bet, my odds locked in at +185 instead. It was a delightful surprise, but it made me wonder how many times the opposite movement had caught bettors by surprise.

The lag in Caesars’ game tracker was high, too. Early in the game, it showed a 5-4 score when the score was 9-4. Every sportsbook with a game tracker lags behind the broadcast, but the Caesars lag seemed longer than other apps.

I didn’t know Gonzaga was going to lose, much less as badly as it did. My return to moneyline betting had proven fruitless. I was down another $10.


When getting started with live betting at WynnBET Massachusetts, I logged into my bank to pull the account and routing numbers for my bank transfer. I finally entered the numbers, hit enter and … nothing.

A message came up that my transaction was in progress and I should check the transactions screen to see if my deposit was successful.

It wasn’t. Nor was my transaction in progress on my second or third attempt at a bank transfer. My debit card was also rejected.

I finally signed up for the VIP Preferred program, which only needed my bank and driver’s license information. My $10 went through, and I browsed the available bets.

This time, I was at a sports bar with my fiancé, and the Creighton vs San Diego State game was on. SDSU was an underdog, but the two teams kept trading points, and neither was too far ahead of the other. I watched the odds for SDSU climb from +175 to +185, then got a last-minute change to +195. I pounced.

Shortly after, Creighton pulled further ahead, and I set my phone down assuming I’d lost another $10. Imagine my surprise when I checked my phone later that afternoon to find that San Diego State had won by one point. There was another $19.50 in another sportsbook account.

Lessons from live betting

I was confident going into this project. My DraftKings Super Bowl win, though small, made me think I could manage a bankroll across six sportsbooks.

Instead, experience reinforced a hard lesson for many bettors to swallow: Randomness comes in streaks. Flipping a coin 1,000 times may result in roughly 500 heads and 500 tails, but there will be streaks of one or the other that seemingly defy chance.

My first three wins were chance events where the games went in my direction. Live betting improved some of my potential payouts, but sometimes the odds moved against me instead.

If Massachusetts sports bettors can get past clunky deposit processes, they’ll certainly enjoy live betting. I had never heard of James Madison until this article, and my Barstool Sportsbook wager made me interested in them.

Live betting is easy to do anywhere, which is its best and worst feature. It’s a great way to interest the whole table of friends, but it also shows why a universal self-exclusion list would be a wonderful responsible gambling innovation.

RELATED: Ranking My Personal Experience With All 6 Sportsbook Apps In MA

If you or a loved one is experiencing problems with gambling, call 1-800-327-5050 or visit www.mahelpline.org/problemgambling to speak with a trained specialist for free, 24/7

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Chris Gerlacher

Christopher Gerlacher is a lead writer for Play MA. He is a versatile, experienced writer with a portfolio that ranges from political and legislative pieces to sports and sports betting. Gerlacher is a devout Broncos fan, for better or for worse, living in the foothills of Arvada, CO.

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