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How to win online contests

Want to win a fabulous prize? The odds are better than you think.

By Donna_Freedman Jul 10, 2012 11:12AM

Image: Happy Man (© Steve McAlister/Brand X Pictures/PictureQuest)A few years ago, I interviewed a group of "sweepers," folks whose hobby is entering contests and sweepstakes. They routinely won things like cash (as much as $100,000 at a clip), savings bonds, jewelry, tech items, vacations, cars, furniture, toys, concert tickets and free gasoline.

My favorite was marketing consultant Noah Fleming, who for a time entered up to 30 contests a day. Here's a sampling of what he scored in just two years: a 46-inch LCD television, a home theater system, DVD box sets, a Wii, a Flip Mino HD camera, two Xbox 360s plus games, an all-expenses-paid trip to the Montreux Jazz Festival in Switzerland, concert tickets, a 20-inch iMac, an autographed hockey jersey, an iPod, a Tassimo coffeemaker and two Dell laptops.

But that's not the best part.

As a Canadian, Fleming didn't have to pay taxes on his winnings the way his neighbors to the south do. It was all his, and it took only about 15 minutes per day.

"I was able to do this at the same time I was catching up on blogs and sipping on my morning coffee," he says.

That's because the Internet has made finding and entering contests and sweepstakes incredibly easy. Back in the day, sweepers lived and died by "the three Ps": patience, persistence and postage. These days it takes only a few strategic keystrokes.

Want a shot at winning? Read on.

Improving the odds

Although I'll be using the terms interchangeably, a "contest" requires some type of skill (often as simple as downloading a picture) whereas a "sweepstakes" is purely a game of chance.

Sweepers often enter both. One woman I interviewed does up to 400 contests every day. Programs like RoboForm make filling out all those entries a cinch.

The truly dedicated improve their chances in other ways, too. They know it's often easier to win local contests and blog-based giveaways than a nationally advertised sweepstakes. You can search for blog contests at a site called Prizey.


Second-chance drawings also have relatively few entries, so savvy sweepers type "second chance drawing" into online search engines or set it as a Google alert. (Post continues below video.)

Where else do they look?

Companies sponsor contests to draw attention to their products and services, promote new items and encourage brand loyalty. But they also want your contact information, so create an e-mail address just for contests. Even if you don't win, you'll be hearing from them.

When a sweep is a scam
The Internet is rife with fraudsters, so heed these tips from the contest pros:

  • Be super-cautious about "Congratulations!" emails for sweepstakes you don't recognize. (Diehard sweepers keep spreadsheets or other types of records.)
  • Alerts for contests from other countries are best deleted. So are any with poor spelling and grammar.
  • It's a scam if you're asked for bank account info or a credit card number.
  • Should you have questions about a contest announcement, visit the sponsor's home page or Facebook page -- and do it directly, rather than clicking on a provided link.
  • Other uses for prizes include giving them as birthday or holiday gifts, selling them on eBay and donating to toy drives and charities.
  • Finally, remember that you must pay taxes on your winnings. Pay as you go, because the Internal Revenue Service will find you.

Do you enter contests and sweepstakes? Have you ever won?

More from MSN Money:

Jul 17, 2012 5:27PM
I learned this tip from our IT guy...on suspicious e-mail links...just use your mouse and HOVER over the link (do NOT click it!)  The actual URL for the link appears and that is where you will go if you click on it.  It's amazing!  I've had these kinds of e-mails appear sporatically, and this works every time.  The URL that appears will be completely unrecognizable! 
Jul 13, 2012 12:31PM
I have been entering and winning contests and sweepstakes consistently for 25 years now. You can read about the prizes I have won in some of my Blogs ( and on my website at This is the most incredible hobby imaginable! With sweepstaking anything is possible!
Sep 5, 2014 9:48AM
We're having a real contest in September 2014 for a new mattress and 5 x sets of sheets.  VCisit our site at or go direct to enter here:

Its real - we're not spammers or phishers - just an A<erican Mattress company now in our 4th generation trying to offer a special opportunity for all Americans.

Good Luck! - Michael
Dec 31, 2013 3:37PM
You can also get free stuff from
Jul 19, 2012 7:44PM
I know a great danish site for entering really cool contests, you can go to to enter some contests + they always update the site with new contests...
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Donna Freedman's Frugal Nation blog is for readers who want to live cheaply -- whether due to necessity or a lifestyle choice. It explores living sustainably and making life more meaningful at the same time.


Donna Freedman

Donna Freedman, a writer based in Anchorage, Alaska, writes the Frugal Nation blog for MSN Money. She won regional and national prizes during an 18-year newspaper career and earned a college degree in midlife without taking out student loans. Donna also writes about the frugal life for her own site, Surviving and Thriving.