How to Win Online Sweepstakes and Contests

I would like to share some things I have learned about entering online sweepstakes. Here are a few tips:

Get a Form Filling Program

Getting a form filler is probably the single best thing you can do to start with. It will make the difference between being able to enter 20 sweepstakes an hour and being able to enter 120 an hour. I'm not exaggerating. Every time you enter a contest you need to type your name, address, phone number and other information about yourself. With a form filling program, you simply click a button on your web browser toolbar and the forms are completed for you automatically. Google includes this feature on their free toolbar that you can download here. I use the Roboform program that you can get here. Both these programs add a tool bar to your web browser (Internet Explorer, Firefox, Mozilla or whatever). If you haven't done this yet, do it now!

Enter the Daily Entry Sweepstakes Daily

This is really the only legal way to give yourself an advantage over others for those sweepstakes that award their prize through a random draw. Think about it for a second. If you and I both enter a draw that allows only a single entry per person, we both have an equal chance of winning. But if you enter a sweepstakes that allows daily entry and you enter it only once while I enter it every day for a month, I'll win 30 times as often as you. Here's another way of looking at it - 10 people enter a daily entry contest, 8 of them enter once and 2 of them enter every day for a month. When it comes time for the draw, 60 of the 68 entries belong to the 2 users who entered daily. Who do you think is going to win? The numbers I used for that example aren't realistic but you can change the numbers and the math remains the same. All serious sweepers understand this - and if you really want to win something, you're better off spending your time entering a small number of daily entry sweeps on a regular basis than entering a large number of single entry ones. If you are a casual sweeper and you're only going to enter draws once in a while, stick to the single entry ones - that way you will have the same chance of winning as me and my hard-core friends.

Get Organized

If you are going to take my advice above and start entering daily sweepstakes, then you need to get organized. That's where the Contestgirl website can really help. While I hope this website is useful to all users, I have built some features that cater specifically to serious sweepers - I call it MyContests. The MyContests feature is described in detail here but briefly, it allows you to create a list of those daily sweepstakes you want to enter on a recurring basis and it keeps track of when you last entered each one to ensure you don't enter too often and risk being disqualified. The MyContests feature comes with something called the Presto button, which is a button on the top of the page that, when pressed, will open 10 sweepstakes forms simultaneously, each in their own window or tab. The Presto button is a huge time saver when you're chugging through your daily list because it lets you spend more time entering sweeps and less time waiting for webpages to download. There's more to MyContests - like allowing you to add private notes to the sweepstakes lisings and allowing you to create a private list of sweeps that may not be listed on the Contestgirl website - you'll see what I mean if you give it a try. You need to sign into the website using a username and password to use MyContests. I know a lot of people don't like having to sign-up for things but it's the only way to make it work because each list is personalized and the website needs to know who you are in order to deliver the right list to you. Any information you provide when you create a username and password will be kept confidential and you will not be put on any mailing lists because you sign-up. In any case, whether you use MyContests or not, my main point here is that you need to find some way of organizing yourself if you want to become serious about entering online sweepstakes.

Sign Up For the Contestgirl Newsletter

I'm not trying to turn this tips page into a sales pitch for the Contestgirl website but the whole purpose of this site it to help you win online sweeps and the newsletter is a big part of it.

The newsletter is an email that I send out once a week and in it I highlight any contests that I think are particularly good. I spend many hours every day looking for the best online sweeps and I see hundreds of them. In the newsletter, I point out the ones that I think are the best. The other thing I do in the newsletter is give you a list of the most popular and the least popular sweeps over the past week. I keep track of how many people click on each of the sweepstakes that I list so I know the ones people like the most and I know the ones they like the least. Most people don't have time to look through all the items that I put up each day so the list of the most popular is a good summary of the big ones that you don't want to miss out on. The list of the least popular sweeps is even more interesting. There are usually some really nice ones that for some reason don't generate that much interest. You should enter these because they are possibly low entry draws, which means good odds of winning.

You can sign-up for the newsletter here. I think you'll find it useful and a lot of fun, but if you ever get tired of it, you can unsubscribe with a single click.

Essay and Photo Contests

Any giveaway that requires you to take a photo, write an essay or something similar is going to get very few entries and anyone who does enter will have great odds of winning. There was a contest from a Ford dealer where the prize was a new car but you had to upload a video describing why you should win. They got a total of 13 entries. That contest used public voting to decide the winner so I'm not surprised that only people who had some talent in producing videos decided to enter. There are some contests, however, that require you to upload a photo or an essay but the winner is decided through a random draw - that is to say, your photo or essay isn't voted on or judged. These are the ones you should jump on when you find them. Most people will see they have to do some work to enter so they will skip it and move on to the easy entry sweeps. I have entered some of these in the past and I won a nice one a few years ago.

Find Local Giveaways

Don't restrict yourself to the sweepstakes you find on the Contestgirl website. I want to keep this site interesting to a large audience and so I only list sweeps that are restricted to a single city if it's an exceptionally good prize. Local contests are great, however, and usually have good odds of winning - I often enter local giveaways and I've won quite a number of times. To find local contests, search Google or Bing for a list of websites of newspapers and radio stations in your town. You'll find these websites often have a page listing their current sweeps.


You'll find that you'll get quite a bit more email once you start entering sweepstakes on a regular basis. It isn't as bad as it used to be because there are stronger laws now that require companies to provide an unsubscribe link on their mailings and require them to notify you before they can add your email address to their lists but you'll still find that it can build up over time.

Most people who enter a lot of sweepstakes will have an email address that they use only for sweepstakes. I recommend that you do that - don't use your everyday email address. You can easily create an email address for yourself using free services like hotmail or gmail and that's what you should be putting into the entry forms.

Always Read the Rules

It's very important that you understand the rules before you enter an online contest. Some sweeps are regional and only allow entries from certain cities or states, some require you to be a certain age, some allow only a single entry while others allow you to enter multiple times, some allow you to enter yourself, your husband and your children while others allow only one entry per household, and so on. I try to point out many of these things when I write up a listing but I make mistakes. You really should read the rules before entering any sweepstakes to make sure you understand the restictions and for a description of what you're signing up for.

Thank the Sponsors

This brings me to the appreciation for the sponsors of all these great sweepstakes. Where appropriate, you should make every effort when you win a contest to thank the sponsor verbally or in a letter. I think it's wonderful that all these businesses are willing to give away all those awesome prizes and think we should be encouraging them to continue by making sure they know how much it is appreciated.

Have Fun

You will win if you keep trying. I don't have the time to enter sweepstakes like I used to but when I did I would spend about an hour each day. I won multiple times each month. Sometimes things would be a little slow but then I'd get an email telling me I've won a camera or an Xbox or a trip and it sure feels good. Keep trying and have fun - I'm telling you, you will win.