Little Gray Squirrel How to win radio contests.

How I Win Contests, Including TWO Trips to Disneyland

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Little Gray Squirrel How to win radio contests.
Winning two $25 Disney Gift Cards was the first step in winning the Grand Prize Trip to Disneyland!

I love contests.  I have been a fan of entering them since I was a kid.  I even remember having a booklet of mail-in contests back before the internet.  I enter (and have won) contests of all types; mail-in, online, entering codes, instant win, collect & win, recipe, call-in, social media, pretty much any kind.  I have yet to enter an eating contest, but I might try if they were giving away a trip to Disney.  I prefer contests where there is an element of skill, like in recipe contests, but I have been lucky entering random drawing contests as well.

I really appreciate the opportunity that companies and brands give to enter contests.  Even though I have won a number of times, it is such an extraordinary experience to win a prize.

The tips listed here are just from my experience.  I wish they could, but they do not guarantee that you will win a contest.

To share my love of contests, I have compiled some tips that have helped me win the following:

Cash          Gift cards          Gift basket

TWO trips to Disneyland     Trip to Portland, OR

A pool float that looks like a pack of string cheese

Food          Lottery Tickets

I even won a t-shirt from a can of soda in a vending machine (I didn’t claim it though and I always wish I would have)

Little Gray Squirrel Foster Farms Cook off
In addition to the awesome Foster Farms Chef’s Coat and a trip to Portland, my recipe won “people’s choice” and I was awarded a gift basket of local food items.

Recipe contests are definitely a favorite of mine.  I have entered many, and received prizes from a couple.  Let me know in the comments if you wan tips on recipe contest best practices in the future.

Top Tips for Winning Radio Contests and Sweepstakes Prizes

Here are my top 7 tips to win contests and sweepstakes

  1. Read the rules.  Always read the rules.  This can almost be its own post but I will highlight what I look for.
    1. Am I eligible? This can be based on age, where I live, who I work for, have I won something from the sponsor before, have I bought or used the sponsor’s product (see more on that below), etc.

      For example, I am not allowed to win a contest from iHeart radio for 1 year due to winning the Grand Prize trip to Disneyland, but I am totally OK with that.  Another example, I am ineligible for some recipe contests (like the Pillsbury Bake Off) because I used to be a professional chef.

    2. What is the start and the end date? Dates of the contest are especially helpful if the contest allows daily or multiple entries. It is also important to know the end time of the contest. Be sure to check what time zone the end of the contest is in.
    3. How often can I enter?  Some are only once, some are once per day, some are more often.
    4. What is the method of entry?  Call-in, online entry, mail-in, watch a show for a keyword or phrase, or a combination of steps.  Mail-in entries can have very specific instruction for the size of the postcard and/or envelope and almost always require handwritten information only.  Pay close attention if you are entering a mail-in contest.
    5. Is there a way to enter without making a purchase?  Also called AMOE (alternate method of entry) This could be a way to email for a code, enter by mail or another method of entry and depending on the prize could be worth the postage.
    6. When, and how I will be notified? (email, phone call, social media message…) so I can be on the lookout.
    7. What is the prize and how much is it worth?  Contest winners are responsible for paying taxes on the value of the prize.  It is easy for a cash prize, just save some of the cash, but you want to make sure you can afford the taxes on a trip, new car, or free-coffee-for-life type of prize.
    8. Winners List.  If you are really curious, there will be instructions, which usually involve you mailing a SASE (self-addressed stamped envelope) to receive a list of prize winners.  Some contests have an online list of winners.
  2. Write it down.  If you are given a cue to call, a time to call or a phrase you have to say, it is a good idea to write down the information, especially if it is a week-long contest or longer, the phrase or song of the day can get mixed up.
  3. Set your TV to record.  If a code or phrase is supposed to air at a certain time, set it to record so you can skip forward or back it up to get the information you need.
  4. Create a contest entry sheet. Use excel or a google sheet with the following information: a link to the contest entry, link to the rules, how often you can enter, prize, and contest end date if you want an easy way to enter multiple contests daily.  The link to rules helps you to be able to go back to see when the prize notification happens or any other questions you may have since some contest pages are no longer able to be accessed after the contest ends.  When you have a couple of minutes during the day, open the spreadsheet to click the links to the contests and quickly enter each one.
  5.  No Purchase Necessary.  I am not a lawyer, but it is my understanding that a company can not require you to buy their product in order to enter their contest.  I again suggest you always read the rules (see above) because you may find an alternate method of entry.  For example, if you can get a code to enter inside a product package, the rules may tell you how to enter the contest via mail or email to receive a free code or entry.
  6. Enter Contests.  I know this seems basic, but the old saying, “you can’t win if you don’t play” is true.  So get out there and enter some.
  7. Don’t waste time. There are plenty of contests out there. Only enter contests important to you with prizes you want to win.

Believe in Luck

Something I just don’t want to hear is people who say they aren’t lucky.
I 100% believe that if you feel you aren’t lucky, you won’t be lucky.
I actually created a pretty floral graphic that says Lucky because I feel it. I am not saying that buying it will make you lucky but feeling lucky is important. And not only for contests but for life in general.

You can get the mug from my Etsy shop.

Tips to win radio call-in contests.

I have won four radio contests over the years.  A combination of luck and planning have helped me win, along with these tips:

  1. Program the phone number into your phone before the contest starts for quick dialing.
  2. Write down any “song of the day” or “phrase or code word” etc. so you don’t forget it in the excitement.
  3. Listen to “live” radio (in your car, an alarm clock radio, a stereo, just a regular radio).  Streaming a radio station is awesome for everyday listening, and fine if you are just getting a code word or song to listen for later or even a “caller 100” contest.  But if you are trying to be caller 10 when you hear the “cue to call” or at the start of a specific song, they may have their 10th caller before you even hear the cue.
  4. Plug in your earphones to your phone so you can hear the busy signal/ring without having to put the phone up to your ear.
  5. Some iPhones have a “call busy redial” button. Use it if you have it. My husband’s does, mine doesn’t.
  6. Use multiple phones to call. Either hold a couple or have your significant other and/or kids dial with you.
  7. Don’t give up too early.  Usually, the winner is announced on the radio after the commercial break, so wait until you hear it, or at least wait a bit longer than you think it may take to get through all the callers has passed.  A contest where you have to be caller 100 can take 8-10 minutes to get to the 100th caller if it goes smoothly, it could take longer.  A contest where caller number 10 wins, can take less than a minute. On a recent “be caller 10” contest, I was using two phones and the lines were busy right off the bat. I thought for sure the lines would be full and I had missed out. I kept trying though, and after dialing four times, both phones started ringing through at the same time. On one phone I was caller 8 and the other I was caller 10!
Little Gray Squirrel how to win a radio contest using two phones
Serious stuff here: me, dialing to win a radio contest using two phones

I have had better luck with radio contests that run at odd hours or require extra steps.   For example, many years ago, I won $50 in lottery scratch-it tickets one morning at about 5:00 am (one benefit of having to work early).  The two Disneyland trips I have won required extra steps beyond just calling when it was time.  The first, I had to watch a morning news program to get a phrase.  Then I had to listen at a certain time, be caller 10 and say the phrase.

Little Gray Squirrel how I win trips to Disneyland
The Disney “Phrase of the Day” scribbled on a post-it was my ticket to win a trip for four to Disneyland.

The second time I won a trip to Disneyland, I had to listen to the radio at a certain time (which was kind of early) to hear the “song of the day”.  When the song played (which could have been anytime over a nine-hour period) I had to be caller 10 to win two Disney gift cards.  Then, on the Friday of that week, one winner of the five from Monday-Friday won the grand prize trip to Disneyland!

Little Gray Squirrel picking up Disney trip prize at iHeart radio
The Boys and I went to K103, iHeart Media radio station to pick up our Disney gift cards and sign the 1099 tax form for the Grand Prize Trip to Disneyland!

Sometimes when you win a trip, it can be months before you actually travel.  A couple of years ago when I won our first trip to Disneyland, the contest was at end of March but after paperwork, selecting travel dates and getting everything set it, was October when we went.  Which was pretty awesome because Halloween Time at Disneyland is so fun.

Grand Prize Trip to Disneyland for the 60th Anniversary

This second trip was different though. We won a trip to Pixar Fest at Disneyland. As a stipulation to winning the prize, we had to be able to travel on specific dates which were only a few weeks from the contest. A radio host traveled with us along with other contest winners from our area.
The gate at the airport had a photo wall and snacks and the whole Alaska Airlines Flight was decked out with Pixar Pier swag.

My family at Disney California Adventure with Mr. Incredible and Elastigirl wearing our contest winner credentials.

I had been following all the fun changes that have been made at Disney California Adventure with the new Pixar Pier.  I even made a pair of Mickey Ears celebrating the movie UP.

Suggested Reading

Learn more tips for entering contests, manifesting, and the Law of Attraction or just like to read exciting uplifting stories? Take a look at these books:

Contesting: The Name It and Claim It Game by Helene Hadsell edited by Carolyn Wilman

Manifest Your Millions!: A Lottery Winner Shares his Law of Attraction Secrets by Eddie Coronado

Some of my favorite contests to enter are:

Radio Contests K103 an iHeart Radio station is not only a favorite station of mine to listen to, but they also give away trips to Disneyland a few times a year.

HGTV Dream Home Giveaway every January, and they also have lots of other contests throughout the year.  Click here for HGTV sweepstakes to enter.  You can enter your email address to receive a notification when the contest starts.

Starbucks Win for Life which usually happens in December but they have had one during the summer as well.  This is a fun game of collecting icons and is one where you can collect them without making a purchase.  Check the Starbucks website to see if/when the contest starts and read the rules for details.

Monopoly collect and win at McDonald’s and Shop Play Win Monopoly game at Albertsons, Safeway, Randalls, Tom Thumb, Vons, Pavilions, ACME, Jewel-Osco, United Supermarkets, Shaw’s, Star Market and other regional stores.  For this one, you collect game pieces when you go shopping.  Kind of a fun reward for doing a chore if you ask me, and we got quite a few free food items, and $5 and $25 store gift cards for playing.

How to find contests to enter


A great way to find contests and sweepstakes to enter.  Google “sweepstakes for cash”, “Disneyland/Disney World Contest”, “grand prize contests” etc. Just make sure they are legitimate (the rules are a good indicator). There are a number of websites that specialize in contests to enter.  Here are some I have used:

Product packaging

At the store, look for packages with contests on them.  They may also have merchandising displays with tear off entry form sheets or contest info.  Popular contests in this category are the Lay’s Flavor Contest and the My Oreo Creation Contest.

Coupons in the newspaper

I found out about the Frigo String Cheese contest in a RedPlum coupon insert in my Sunday newspaper.  I think the grand prize was a tropical vacation.  I didn’t win that, but it was a fun contest where you got to play a matching game.  I played at the right time and instantly won this awesome pool float.

Little Gray Squirrel Contest Prize I Won
How fun is this Frigo String Cheese pool float!

Entering Contests on Social Media

Keep an eye out for legitimate contests online.  There are numerous bogus contests out there so make sure you read the rules and look into the sponsor and the company running the contest before entering.  Disney contests are extremely popular.  I have seen a fake Disney Facebook page offering a contest before.  The prize may or may not have been real, but since you usually have to enter your personal information, be sure the source is safe.

Entering contests on social media is usually quick and easy. On Instagram they usually ask you to follow the sponsor and maybe another page that is involved in the giveaway and leave a comment and/or tag a friend. It is good to have a list of friends that you have asked if it is ok if you tag them for contests so you don’t upset your friends.

I have won two contests on Instagram.

The first social media contest I won was a $300 box of craft supplies from Lia Griffith. It was such an incredible prize. All of her products are so beautiful and top quality. I actually recorded an unboxing of the prize. You can watch it here on my YouTube channel.

The second prize I won on Instagram was a selection of stationary, journals, and stickers from @3birdsdesign. I love their products too and was just thrilled to win. An important note. I was actually the alternate winner for the stationary prize. The first winner did not reply in the stated time to claim their prize.
It is very important to make sure you keep an eye out for how the company will contact you. Read the rules. For this contest, they said they would contact the winner via DM on Instagram.
For big contests, I will put a note on my calendar to check my spam email

Subscribe to email lists for contests

If there is a company that runs contests regularly, be sure to subscribe to be notified of future contests.  This could be radio stations, news stations, TV channels like HGTV as mentioned above or stores like Cost Plus World Market.

Finally, when entering contests and sweepstakes of any kind, remember, the reason companies offer these is to raise awareness of their brand or new products and to collect contact info for their mailing list.  I think that is great, and as I mentioned, I appreciate the opportunity to enter, just make sure you un-check or don’t check boxes that will sign you up for mailing lists if you do not want to be part of those.  I may be in the minority, but I do not have a separate email address for entering contests.  You certainly can, but the main reason I don’t is because I want to be notified if I win.  I am also not overly bothered by junk mail, I just delete it and unsubscribe if it isn’t something I want to receive. A lot of the contests I enter are for companies and products I do like, so receiving coupons and notifications about offers and sales from them is ok with me.

Express gratitude when winning contests

Try to reach out to the sponsor of the contest through their website or social media to thank them for the prize. If it is a larger prize you will probably get the contact information of the person handling the prize delivery and forms. Send them a thank you note.
You can also photograph and share the prize on social media and tag the company.

The universe is always listening and gives back what you project.

And remember, always follow the rules!

Do you enter contests?  What prizes have you won?  I would love to hear about it, leave a comment below.

Share these tips with people you know who want to win contest prizes!

Good Luck!


This post is not sponsored by and I am not affiliated in any way by any of the companies mentioned above at the time I entered these contests, I am just a fan of entering contests and want to share my experience with you.

Please read our disclosure policy for more information.


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