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How To Win Entering Mail In Sweepstakes

Updated on November 2, 2008

Ever watch and wonder how some people can win money and prizes all the time and you never seem to win anything? Do you enter sweepstakes? You can't win if you don't enter!

I got into online and mail in sweepstakes years ago with the help of my grandmother. She had a mail in sweepstakes newsletter delivered once a month that listed a current list of mail in sweepstakes she could enter. After watching her win hats, cameras, t-shirts, cash, Nintendo and other video games, and more, I was kinda of interested but it wasn't until she won the $15,000 diamond ring that I really took notice. I wanted that ring!

I started by filling out some of my own entries using her sweepstaking supplies. I had no idea that there was a vast wealth of information related to sweepstakes on the internet. What she paid $35 a month for in a 10 page newsletter could be found easily with a little searching on the internet.

Since then I have been doing online and mail in sweepstakes on and off and from mail in and online sweepstakes some of the bigger ticket Items I have won are a stereo, a digital camera, concert tickets(twice in one summer), Microsoft Publisher software, XBox 360 games and a $200 visa gift card.

The little things are what keep you motivated in this hobby. My winnings include DVD, beauty products, a remote control, Smaller gift certificates wins have been around from $5 to $50 in value, cd holder, tons of free candy coupons, food coupons, and drink coupons and a whole lot more. In total I have won over $2000 in sweepstakes prizes

It's relatively easy to get started. There are three ways to go. Online sweepstakes, phone in sweepstakes, and mail in sweepstakes. You can do one, the other, or both. Here's how to do the mail insweepstakes entries.


When you're getting started a good idea is to put together a box for all your supplies in side include the following.

  • Envelopes

Most snail-mail sweeps require white #10 envelopes (the long ones). You can buy a box of 500 at places like office depot for around $6. For snail-mails that don't require the #10's you can use the smaller ones or make your own out of wrapping paper, colored paper, or anything else that will be sturdy enough. Greeting card envelopes also work great.

Some sweepstakers use different colored envelopes if white is not required. Some think that by having one that stands out you will have a better chance of yours being chosen. I have not noticed a difference but try it yourself if your interested.

  • 3x5 index cards and paper

For around $2 you can get 100 index cards. Some sweepstakes require paper some ask for a card. It is difficult to find 3x5 paper except from sweepstakes supply online shops. If time is an issue you can order from these, but otherwise make your own with computer paper

  • Postcards

A handful of sweepstakes want you to enter using postcards. This can get expensive if you are buying not only postcards but also the postage for them. At the post office you can get blank postcards for only the price of shipping. These work just fine and are totally acceptable.

Another option is to go to garage sales. You can find stacks of postcards for really cheap bundled together. If this isn't an option try cereal or other cardboard boxes. Cut them out into 4x6 squares and write on the blank side in dark ink.

  • Stamps

How many to buy will be dependent on how many main in sweepstakes you think you may enter. Purchase more ahead of time so you do not have to make it to the post office before deadlines.

  • Black and blue pens.

Some sweepstakes require the entries be filled out in only blue ink, some require black. Most require they be filled out in either of the two. Avoid different colors. They may be more colorful but they can get your disqualified from the contest.

Finding Mail In Sweepstakes To Enter.

Grocery and drug stores sometimes have entry forms located within in the isles. Pick a bunch of them up if the directions say more than one entry. Check on your food packages at home. Many snack and cereal products have sweepstakes printed right one them

Go online using or any other search engine type, in snail-mail sweepstakes or mail-in sweepstakes. You can find quite a few using this method but I find it easiest to subscribe to a newsletter. There are a variety of sweepstakes newsletters you can purchase on the Internet.

I've odered SweepSheet in the past. There are not as many mail in sweepstakes to enter as with Winning Ways, but the listings are for the sweepstakes that you will have the best chance of winning.


How to Increase Your Odds Of Winning

I like to enter sweepstakes that have multiple prizes. I'll enter at least once for those with just one prize but if there are say (1000) $100 prizes being given away, I'll enter this one as often as I can afford as long as the sweepstakes allows it. Some sweepstakes can have around (50,000) prizes. I enter as many as I can for these and the wins are usually small ticket items but they keep you motivated and can make great gifts. General rule of thumb. If there's more than 1000 prizes being given away. Enter as often as the rules allow!

Things to know

Sweepstakes judges have the reputation for being tough here are some things you have to know to keep from getting disqualified.

  • Pay attention to the address for entering

Do not stray and get lazy. Print the entire address as posted in the newsletter, website, or package. If the address is printed in block letters then write in block letters on your entry.

  • Age limits

Most require you to be 18. But Age limits vary from sweepstakes to sweestakes. For alcohol related sweepstakes the age limit is generally 21. Kids sweepstakes can vary so pay attention if you are entering your kids names.

  • Method of entry

Only enter using what it asks for. Does it want paper, card, postcard? Some may say paper or card. If the prize is something you really want, read the directions closely. Many sweepstakes have multiple ways to enter. Use them all.

  • Time of entry

Look for entering and ending dates. They will either say postmarked or received by on the sweepstakes. Make sure your entries arrive on time and before the end on the contest.

  • Amount of entries

The amount of entries you can send in will depend on the sweepstakes. IT may all Daily, weekly, monthly, or unlimited. Some allow just one entry. Don't get all your entries disqualified by entering more then allowed.

  • Keep records

I write in my newsletter the dates I entered using just 6/25, 6/26 or whatever date it was. Then I'll know not to enter again until it allows. Also, if you receive a confirmation of a winning, you can look back and see what it was.

Record keeping is also important when you do your taxes. Uncle Sam wants a cut out of your winnings. Speak with your tax advisor for more information on this.

  • Spread out your entries

It is time consuming to write entries all the time. It's a lot easier to do a whole bunch at once. If you write your entries in advance write the date in the right-hand corner where the stamp will go. That way you can save it in your sweepstakes box and spread out your entries throughout the sweepstakes. Especially helpful for unlimited and daily.

Sweepstaking hobbiest generally agree that the best time to submit entries is in the very first days a sweepstakes is open. At this time there will be less entries because less people know about the sweepstakes.


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    • profile image


      8 years ago

      Yea I went to the post office to get the pre-stamped postcards and they looked at me rather puzzled and said "we don't have them". Interesting.

    • profile image


      9 years ago

      i get it now

    • MrMarmalade profile image


      11 years ago from Sydney

      Great hub

      Thank you

    • Research Analyst profile image

      Research Analyst 

      11 years ago

      This is great information, I have never won anything, maybe now I will.


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