This Is How You Win Sweepstakes


The idea of winning something for nothing is appealing. As an avid enthusiast of entering sweepstakes and contests, I have over 15 years of experience and plenty of wins, I can vouch for the hobby as one that can help you obtain cash, trips, gadgets, and more with just the investment of time and patience. For many people, however, a lack of both time and patience leads them to frustration. "Why haven't I won?" many ask — even after just a few weeks of starting the hobby. Here is what I've learned over the years. (See also: How to Win in Online Sweepstakes)

The "Sweepstakes" Cycle Can Be a Long One

Back in 1998, when I started entering sweepstakes, most promotions were administered the old-fashioned way — with a stamp and an envelope. The Internet was relatively new, so most contests were done via postal mail. The time it took to enter, win, and find out about your win could be six months or more. Today, even with the web hosting most promotions, there is still a timeframe of eight weeks or more for people to get their entries in, two weeks for the sweepstakes administrator to draw and verify winners, and eight weeks for the prizes to be mailed out. Before you start complaining that you never win, check to see if it is even possible for you to have been picked and notified yet. (See also: 9 Steps to Become More Patient)

Odds Can Vary by Promotion

Every year, HGTV holds its "Dream Home Giveaway." Millions of people enter the sweepstakes (sometimes every day) to get their chance at being the lucky winner of an amazing property worth millions of dollars. If you were to enter just these types of high-profile promotions, you would likely never see any wins. The odds of winning are so astronomical that you could enter and enter and enter… and wonder if it was worth your time. By entering a promotion that hits the "sweet spot" of many prizes of moderate values, however, you can increase your odds of winning. Examples of this type of promotion could be one that offers 20 prizes of $1,000 savings bonds, a 50-state promotion that gives out restaurant gift cards to one entrant per U.S. state, or an instant win sweepstakes with thousands of prizes each valued at $20 or below. Sure, you won't be a millionaire by the end of it, but even winning a prize with a value of $100 makes you a winner (and can improve your quality of life somewhat).

Disqualification Can — and Does — Happen

It's super important to read the rules of any promotion and make sure you are following them exactly. Most contests and sweepstakes have common regulations that require the entrants to be a certain age, meet residency requirements, and sometimes even have a certain occupation. Other rules include how many total times you can enter and how many people per household can enter the same sweepstakes. Some companies won't let the same person win more than one time in a given timeframe, as well. If you are entering, but also disqualifying yourself with your entries, you will never see a win.

Use a Form Filler

I highly recommend using a form filler, either as an add-on or extension to your web browser or as a separate software feature, to save time and ensure accuracy for each entry. Using any automated "bot" however, can be detected by most sweepstakes sites and can result in your entry — and all further entries from your IP address — to be disqualified. Reliable form tools include Roboform and the Form Filler extensions for Chrome. (See also: 16 Time and Money Saving Apps)

You Could Be Missing Your Win Notifications

As a blogger, I run two to three giveaways on my site each month. Each time, I notify the winner at the email address they give in their entry. One out of six times, however, I send multiple notifications and never hear back. This tells me that winners are either typing in the wrong email on their entry forms, or they are not checking their email on time, or emails are going to spam and being tossed. Make double-sure that you are providing the correct info on your entries, and always check daily — even in your spam folder — for winning notifications. Nothing is worse than finding that special email after the timeframe for claiming your prize!

While I personally don't enter giveaways that don't notify winners (but rather rely on the winners to come back and check a winner's list to claim their prize), notifications can be lost. Setting up a Google Alert with the name you use to enter giveaways, as well as the word "winner" can help ensure you get an email when a website lists you as a prize winner. You can then contact the sponsor to see how to get your prize.

A "Winning" Habit Helps

It's much easier to do anything in life if you do it consistently.

Many of the "lifelong" contesters I know have a special schedule to their entering that they follow religiously. While the time of day may not have as much importance as the fact that they commit to just doing their entries, the fact remains that developing a habit ensures many entries. In addition, many entries mean a higher chance of winning. Make entering fun instead of being a chore by tying it to something else you like to do like watching your daily newscast or listening to tunes. The more regular you are with the practice, the more wins you'll see coming in later! (See also: Habits Are the Secret to Happiness)

Some things I've done to help me develop a regular habit include:

  • Sign up for's "My Sweeps" tracking tool. This feature is free for lite users and allows you to save your favorite sweepstakes, as well as check off each time you've entered, along with what time of day your entry took place.
  • Subscribe to email reminders for the most coveted prize giveaways, alerting you to the fact that you haven't made your daily entry yet.
  • Tying your sweepstakes hobby to a favorite pastime you do each day (watching reruns of "Burn Notice" or catching up on the news, for example) gives you a way to do your entries at the same time each day, as well as multitask in a relaxing way.

Luck has something to do with winning, but most people I know that "never" win don't understand the concepts above. "You can't win if you don't enter" holds more truth than any other advice I know on sweepstakes and contests. You can win if you don't give up too quickly.

Are you a sweepstakes regular? What have you won?

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Andrea Karim's picture

Well, I just started doing this with some guidance from another pro, but I'm find it really hard to use the tracking tools to measure what I sweepstakes I have entered. So far, all I have managed to do is accidentally subscribe to Woman's Day.

Guest's picture

Everything you say here is true! I have won lots of sweepstakes, and I've only been doing it 1 year! Last year, I won 2 trips, one to NYC and the other to Paris.

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