There’s no sure fire way to win an item, but here are some ways to increase your chances:

1) Get a fast internet connection – This gives you a better shot of getting your click through

2) Time your click – You can actually click a little early. You’ll see that clicking too early will tell you that the contest hasn’t started yet, but you can click right around when the clock ticks to zero and not get that message. If you’re waiting for it to change to “Now” then you’re already way too late.

3) Choose your items – Items in larger quantities give you a better shot. Obviously the gift certificates are the easiest to get. These aren’t nearly as good as the other items, but the can still save you money.

4) Choose your times – The items at 6pm and 7pm will give you the best shot because they occur when the Eastern part of the country is out of work and fewer people are in front of computers

5) Keep trying – Keep on clicking even after the first minute. Once something hits someone’s cart there are 3 steps each with time limits. If someone misses a time limit or closes their browser the item will go back into the pool. There is a different message for “sold out” than there is for “all items in carts”. Keep trying until you get the “sold out” message.

Now, on with the tips:

Look for sweepstakes with more stringent requirements, for example entries in block (capital) letters. These are harder to enter and more entries will be disqualified, so you should enter them more often since your correctly formatted entry will have a better chance of winning.

You can add a unique border to your postcard entries fairly easily with a pair of craft scissors or pinking shears. It might even help your entry stand out better if the winners are drawn by hand.

If a sweepstakes asks for your email address and you don’t have one, make sure to put that on the entry. Or, you can get a free email address from websites like Gmail or Yahoo.

If your like me and have children, get them to help. If they are older they can help with writing the entries and the younger kids can help you decorate postcards or envelopes.

1. Never, Ever send money for a prize. Almost anytime someone asks you to do this, it is a SCAM. You will have to pay taxes on your winnings, but you should not need to send money first before collecting a prize.

2. Read the rules carefully and follow them to the letter. You don’t want to spend a bunch of your valuable time entering a contest just to have your entry discarded because you didn’t follow the rules. Rules to look out for include requiring handwritten entries, or a specific size postcard.

3. Only enter contests for prizes that you want to win. Again, this comes down to time. If you spend time entering contests you don’t care about you have lost time you could have spent entering contests you REALLY want to win.

4. Smaller contests sometimes have better odds of winning. Sometimes entering many smaller contests is more worthwhile then entering one large contest that everyone and their mother will be entering.

5. Enter as many sweepstakes as possible, but keeping rule #3 in mind at the same time. There are many tools to help you with this, both online and off. See out reviews section for some recommendations.

6. If possible according to the rules, use postcards rather then envelopes. They will be cheaper to send and you can save yourself some money on postage. Again, read the rules. Many times postcards or envelopes need to be hand addressed. There are services that will do this for you if you are unable to for any reason. I talked about them in this article.

7. Enter local contests. Many times these contests follow rule #4. These local contests include raffles at carnivals and fairs, or even dropping your business card in a bowl at the restaurant you just had lunch at. If you don’t have business cards I have a great tip for how to enter those types on contests here.

A company called Vista Print offers FREE business cards on their website. Now you do have to pay shipping, so I suppose I should call this “inexpensive” business cards, but the shipping is pretty minimal and compared to what it costs to have business cards printed normally, it’s a pretty good savings. They also offer a couple of other things for free, like postcards and a rubber stamp, but the business cards are what I want to talk about today.

It’s very easy to design your business card, you can do it all online at their website. You can choose from some pretty nice designs too. You can make up a fun job title to use if you don’t have a “real” one. Make sure to put your real address and phone number on the card so you can be notified when you have won. Once the cards come, take some and put them in your wallet or purse and your ready to enter any and all of those local sweepstakes you have been looking at, and for a nearly free price!

The first items I found were Beginners Packs that include all the postcards, envelopes and stamps one would need to get started as a serious sweeper. These items were reasonable priced and could definitely help out a new sweeper, but I think for the more experienced sweeper, they may not be that useful. By now most of us have found a good, inexpensive source for our sweeping supplies.

Next up is Handwriting service. At first glance this doesn’t seem very useful to me, I mean, we all know how to write. But thinking about it, I realized that for someone who has arthritis, or who can’t write for any reason, this is a great solution to be able to continue to participate in sweepstakes. Also, it’s a great idea for people who are just so busy that handwriting all of those postcards would be impossible. Another great service to keep in mind if your interested.

If you are interested in collectible sweepstakes items, EBay is a great resource for those as well. There are classic Irish Lottery tickets along with magazine and print ads for old sweepstakes. Sometimes you can even find classic entry forms. Some of these would be pretty cool to own for the die-hard sweeper.

As is to be expected, there are tons of people selling sweepstakes stationary that is already modified in a way to make your entry stand out and be fun at the same time. From Hello Kitty to Disney characters, you can get envelopes, postcards and paper all set to add that extra whimsy to your sweepstakes entries. Anything you can do, within the rules of the specific sweepstakes of course, to make your entry stand out can be helpful, and in this case people have done some of the work for you.

• First, create a new tag in Gmail for your sweepstakes email to go to, I like to call mine Sweeps.
• Then click on the “settings” link at the top right of the Gmail page. Choose the “Filters” link when that page loads.
• Now Click on the “Create a new filter” link at the bottom. In the To: field type “YourEmail+YourLabel@gmail.com”, for example mine would be “Win+Sweeps@gmail.com” (not my real gmail account).
• Now click the “Next Step” button. Once that page loads check the checkbox next to “Apply the Label” and The checkbox next to “Skip the Inbox” and choose your new label from the drop down. Click the “Create Filter” button and you are all set.

Now when you go to enter a sweepstakes that needs an email address, you can just use: “YourEmail+YourLabel@gmail.com” and when an email is sent there it will be automatically routed to your new folder. After a while, if you find the new email address is getting anextraordinarily large amount of spam, you can simply change the filter to route any email sent there to the “Spam” folder and create a new email for your sweepstakes entries.

Since I don’t use Yahoo or Hotmail, I’m not certain if they have a similar feature, but if you use one of those and you know how to do something similar, feel free to post about it in the comments!