How to Win Big in Online Sweepstakes


One of our Best Money Tips roundups recently included an article from MSN Money that shared how to win contests and sweepstakes. I’m pretty fascinated by the concept, because entering them is fast, easy, and doesn’t take a lot of thought. Think you don’t have a chance at winning anything? Tell that to Michelle Troutt, a woman mentioned in the article who has won 22 vacations, cash, and numerous other items — all in the past five years alone! True, Michelle admits to filling out nearly 400 sweepstakes forms during each 10-hour shift at her job (which has a lot of downtime), but it seems that a little persistence can pay off for anyone. In fact, Wise Bread’s own Linsey Knerl is a sweeper herself, and wrote about her tips.

Quick side note: sweepstakes are technically games of pure chance, while contests require submission of an essay, photo, or other action on the part of the entrant. However, both the original MSN article and this post use the two interchangeably. Now you know.

Why Do Companies Sponsor Giveaways?

The answer is pretty much what you’d expect: companies put on sweepstakes as a marketing move. The sweepstakes gets their name in the media, promotes brand awareness, and generates excitement. Companies often do a contest related to a new product launch, repositioning, or just to attract more customers. They will also use entry information to collect data on their products’ users. After all, why do you think Facebook is valued at $50 billion? It’s not because they sell a product. It’s because they have mountains of data that are useful to companies.

How to Find Contests

The article gives some pretty good advice on how to find a plethora of contests. For starters, various websites organize contest information in one convenient place. is a free site that arranges sweekpstakes by new, expiring, entry frequency, prizes, and more. Similar sites include Sweepstakes Advantage, Win Prizes Online, and You should also be on the lookout for contests anchored to specific events, such as Black Friday, the Superbowl, and major holidays. To make sure you’re entering contests that have prizes you actually want, look into what interests you. For example, check out the many parenting blogs online for giveaways related to children’s clothing, diapers, and vacations to family-friendly destinations. Other good methods of finding contests including signing onto Twitter and searching for the word “win,” or setting a Google alert.

Strategies for Winning

Turns out, serious sweepers adhere to a number of strategies when it comes to winning big and winning often. Some follow the “enter everything” rule (made MUCH easier with Autofill Forms add-ons — learn how to do using your Google Toolbar). Others are more selective, seeking out only local contests with fewer entrants, or contests with prizes they really want. If you do start winning often, consider selling, gifting, or donating items you can’t use or don’t want.

General Tips

Some of the highlights for having a good sweepstakes experience include watching out for local contests. Because there are fewer entrants, your chances of winning are greatly increased. You should also make sure to follow the contest rules — a contest that says to send in your favorite picture of your dog does not mean taking a picture of your husband dressed up as one. In addition, pay attention to entry frequency. For example, to enter the HGTV dream home giveaway, you can enter once per day at as well as Lastly, if you do win The Big One, don’t forget to include your winnings on your taxes for that year. If your prize is valued in excess of $600, you should receive a 1099-MISC from the company giving the prize away, and you’ll report that as “other income” on your tax return.

Protect Yourself Online

If you do decide to enter an online sweepstakes, there are a few things you should do to protect yourself online. There are a number of scams out there, and some of them may be harder to spot than others. One of the biggest pieces of advice for sweepers is to set up a dedicated e-mail account that you’ll use only for entering contests, and be prepared for the spam to pour in. Be wary of e-mails that congratulate you on winning a contest you don’t remember entering. Also watch out for e-mails asking you to click-through to a website. It’s always a better idea to open a new tab or window and go directly to the contest organizer’s homepage to verify that you’re not following a phony link. Finally, watch out for scam contests that appear to promote a contest in a foreign company, are poorly written or filled with grammatical errors, or ask for bank account numbers or credit card information.

So there’s the long and short of winning sweepstakes online. I don’t know about you, but I think I’ll give it a try for awhile to see what happens. Have you ever won anything in an online contest, or do you plan to try? Share your thoughts in the comments!

Disclaimer: The links and mentions on this site may be affiliate links. But they do not affect the actual opinions and recommendations of the authors.

Wise Bread is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to

Guest's picture
Jessica G.

Just came to say I started doing these last week after seeing the article, and I've already won twice! Neither were very big (probably worth $100 total), but both were things I needed but were holding off buying! Sweeeeeet! Thanks for the article!

Janey Osterlind's picture

Great to hear the tips are working! Thanks for the feedback. Sadly, I did not win the HGTV Dream Home 2011 - but I'm still going to try for other prizes!

Guest's picture

I want to win free vacations and products! But then again, who doesn't? I always see ads for sweepstakes, but to be honest I never entered because I thought that no one actually won anything! I thought so many people apply to them, there for I don't stand a chance. Well after reading this I wont think that anymore! I might have to set aside a day when I dedicate my time to entering some!

Guest's picture

YES I did win a Mustang in a contest!!! Frist thing I had ever won . It was a contest and 25 other people got the answer right as well . I was the one that they pulled the name out of the hat as the winner. Took 4 month's of entry's to win and God's help.