Sweepstakes: How to Win Big – A Guest Post

Being a stay-at-home mother of two, I don’t get a lot of time to myself. I have had to find a hobby that could calm, interest, and remove me from my everyday craziness all in the five minute random spurts that I get throughout the day. The day that I realized this is the day I fell in love with sweepstakes. I LOVE to sweep. I think it is fun, easy, and takes only minutes of your time daily.

I have been playing actively for about a year and have consistently won. With the help of my auto-fill program (you will want to download one free for your browser!), I enter about 60-80 sweepstakes per day. In the last two months alone I have won a $50 gift card to Express, a $125 gift bag from Rachael Ray, a $10 gift card to Starbucks, a $10 gift card to Blockbuster, 3 jars of salsa, $20 cash, a holiday floor rug, an Ipod Nano, and a few other little prizes. All for playing in 5 minute spurts per day.

Sweepstakes basically come in two different forms: Prize Drawing Sweepstakes and Instant Win. When a company has a prize drawing, entries are accepted daily and prizes are mailed out at the end of the sweepstakes period. You will not know you’ve won until you receive a prize. Instant Win games will tell you if you’ve won immediately. Many companies host both at the same time, in the same game. So, just because you didn’t win the Instant game doesn’t mean you won’t get an Ipod Nano in the mail a few weeks later (like me!).

Anyone with a computer connection can play sweepstakes, but there are several things that you need to know in order to win. First, you have to know where to start! There are many websites out there that can direct you to active sweepstakes, but you’ll have to make sure it is a site that is sending you to legitimate places. My favorite site for finding sweepstakes is Sweeties Sweeps. Wendy is awesome and updates daily. She weeds out the sweeps that she recommends and posts the rules to playing. I also do a sweepstakes series on my site, Couponing For 4. I post and update a running list of the most winnable and/or easy sweepstakes to enter. Whatever sweeps referral site you use, though, make sure you investigate the it before giving all of your information. I prefer blogs for that reason – I can read/subscribe fairly anonymously and they don’t require any of my personal information.

The most important key to winning is entering daily. I can’t stress that enough. If you enter a sweepstakes once that is fine, but remember that if you can enter once per day for the entire entry period, there are hundreds of people out there who have eighty entries to your one. Who’s more likely to win?

Next, you have to read the rules. If you are 17 and the sweepstakes requires you to be 18 to win, don’t think that you can scam the company. You will be wasting their time and yours. Make sure to enter sweeps that you can win! There are sometimes other odd rules that you need to pay attention to. For example, the sweep may be limited to only 9 states or the entry period is 24 hours, but it’s based on time of entry during the day instead of calendar day. All things to pay attention to.

Some people feel that time of day is important to winning. If there are predetermined instant win prize times that the company has set, you are more likely to win if you play in the middle of the night because less people are playing. I would have to agree with that, but I have never played in the middle of the night (I have to get through the day with two little kids!) and I am doing just fine prize-wise.

Lastly, have fun with it! No one wins every day and there are very dry weeks. But if you enter every day, don’t expect to win, and play because there is a possibility that you’ll get a nice surprise, you’ll find that you will. Have fun!

Alli is a Chicago-based stay-at-home mother of two who turned to couponing in order to stave off the monotony of the day and found a new passion. She runs Couponingfor4, where she discusses the weekly grocery and drugstore deals, tips for money saving, sweepstakes, and other ways to make extra income.


  1. Cindy's paradise says:

    Ally, thanks for the post. As a sweeping hobbyist for over 20 years, I appreciated your comments and agree with most. I was very surprised, however, by your comment that entering 60-80 sweeps a day only takes a couple of minutes. My auto fill requires me to go to each site, then auto fills the fields. Even then, I have to check the drop down menus, like states, to ensure that they were filled. 60 to 80 entries a day would take me several hours. I use Safari's auto fill, so maybe you have a better one? Thanks for the clarification.

  2. Hmmm how do you only enter for 5 minutes? I feel like I do hours each day!!!!! Congrats on all the great wins 🙂

  3. kalea_kane says:

    What a fun post to read! Thanks for sharing!

  4. Cindy and Becca, let me clarify – it definitely takes more than 5 minutes per day! It takes about an hour total for the 60-80. But many days when I have 5 minutes, I enter a few sweeps. I can do it throughout the day and feel like I've accomplished something and had a little fun just for me. Sorry if I stated it in a confusing way!! 🙂

    Oh, and I use firefox with the auto-fill to save me some time, but I double check everything too!

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