How To Win Contests and Sweepstakes

Win all the contests and make it rain!On any given day, thousands of contests are created to promote goods and services of companies around the world. Someone has to win those contests. Why not let that person be you?

In the last year, I’ve entered numerous contests in order to win fantastic prizes, including tee shirts, high-end backpacks, VIP concert tickets, gift cards, cash, and a $5,000 scholarship. The purpose of this post is not to gloat, but to assure the world that anyone can win with the right techniques and mindset.

While most attribute my contest success to luck (and it is a big factor), I do have a method that I use to increase my chances of winning these contests. I’ve shared some tips below.

1. Choose a contest

Since most contests have at least some form of online presence nowadays, contests are easier to find and enter than ever. A simple Google search will turn up hundreds of contests, but you can select the contests that increase your chances of winning. Just because odds of winning a contest aren’t great, it doesn’t mean you shouldn’t enter—especially if the prize is big enough.

Best Odds Of Winning Poor Odds Of Winning
  • Entry is restricted by state of residence, age, gender, etc.
  • The contest is annoying to enter – it has a long survey or requires multi-page registration.
  • Some element of skill is required to enter. Fewer people even attempt to enter video, prose, or photography contests.
  • Contests that are advertised across the nation.
  • Contests with a small number of prizes awarded compared to entry size.
  • Giveaways with a very long entry period.
  • Contests with unlimited entries.
  • Prizes are not guaranteed to be awarded.

If you find a site that makes entering even easier, like a collection of sweepstakes, bookmark it. For college students, check out CampusLIVE. I’ve won some pretty awesome prizes for playing a few games on the site…

2. Read the rules

All contests have rules, it is your job to read the fine print.** Click To Tweet Most people don’t pay attention to these rules, but they provide several useful pieces of information, including eligibility, odds of winning, and alternate methods of entry.

Sometimes you don’t even have to do the task associated with the contest. For example, if a contest makes you play a game before submitting your entry form, it may be possible to bypass the game and simply submit the form. This saves time and effort that you can use to do other things—like enter more contests.

3. Enter

After you determine what kind of contest it is (skill contest, sweepstakes, voting contest) you can develop a strategy to enter.

  • Skill contests — These are by far my favorite kinds of contests. They include design contests, sending in recipes, and video submissions, to name a few. Because they require creativity and a bit of effort, the number of entries can be much smaller than normal sweepstakes. Increase your chances by making your entry stand out, since humans determine the winner. For example, when the contest calls for crafting a tweet, include a visual component (like TwitPic) to make the judge stop as they are scrolling through submissions and look at your entry.
  • Sweepstakes — I would recommend having a separate email account that is dedicated solely to entering contests in case you get spammed, but I know that is simply impractical for most. In that case, be wary of sites that ask for this information, and only give it if you trust the site. Reading the rules and privacy policy will help you understand which sites don’t give information to third parties. For sweepstakes… enter, enter, enter.
  • Voting contests — These are a kind of skill contest that also requires creativity and effort, but the winners are determined by the voting public. Making entries stand out is crucial here too, and can be achieved by tailoring your submission to the voting audience. When college students are the judge of a contest, put yourself in the mind of a college student—as scary as that may be—to enter appropriately. Additionally, use your social networks to get friends and family to vote for you if possible. Be aware that spamming the link is frowned upon and can do harm to your cause, but providing a story or specific reason why your close friends and family should vote for you will help—and they can share that story with their networks too, getting you more votes.

4. Keep a positive attitude

You are not going to win every contest or sweepstakes you enter. If you do, buy a lottery ticket for me, would you? It is important to not get discouraged while entering and to keep entering away.

Finally, to quote the great Wayne Gretzky, “You miss 100% of the shots you never take.” You can’t win if you don’t play! Best of luck to you in your contest-entering ventures!

Have you ever won something from a contest? What tips would you add? I look forward to reading your comments below!

Until next time,


**If you can’t read the fine print (or find it anywhere) be very cautious! That may be a sign the contest isn’t the most legitimate. Now go back up and read the rest of this post!

About Andrew Grojean

Andrew is a Social Media Manager at a digital marketing agency in KC, interested in all things social media, pop culture, sports, and technology.

Check Also


One Second Every Day: Vol. 4 (2017 Highlights Edition)

In 2017, I traveled back to New York, ate my way through Nashville, and cruised …


  1. It’s Rock and Roll Thursday, Have a Super Night!

  2. Nice summary.

  3. Nice description.

  4. I did enter the Lottery tonight it is over 500 million. Hey you never know, someone has to win.

  5. Good to know, thank you very much

  6. Nice article !! Thanks for sharing !!

  7. Thanks Andrew for sharing! I’ve recently read on a blog that you can influence your luck by Joan Ginther, the lottery queen, a Texan woman who is the most fortunate person in the world, as far as winning lotteries is concerned. Since 1993, this is the fourth win of Joan Ginther in the Texas lottery, which makes her the owner of $20.4 million. Have a great and happy Friday! Best, Lucas

  8. just shared it a lot

  9. Way cool. Thanks for the information.

  10. I always use this site, where I someday hope to win the big prize 🙂

Leave Andrew a Reply