Cost of Living

How to beat the odds when you play contests

A well-organized, contest-entry system is the key to winning often, experts and contest enthusiasts say.

Hint: You can't win if you don't play

A Tims cup with old Roll Up the Rim logo
Tim Hortons Roll Up To Win contests have not involved rolling up a rim since 2020, and instead have been conducted through a mobile app. (Nathan Denette/The Canadian Press)

It's true what they say: you can't win if you don't play. But people who win a lot of contests say they take their playing very seriously when it comes to winning free prizes.

They add It also means being strategic about giving yourself the best chance of winning — and maybe even pushing the limits of what you're comfortable doing to win a prize.

Elaine Douglas, from Beamsville, Ont., wins contests so often she sometimes loses track of all her prizes.

"It sounds so silly, but yeah, it gets to that point that things start coming in the mail and you're like, 'Oh, I totally forgot about that one,'" she told Cost of Living.

This can happen when you enter up to 500 contests a day — yes, a day — like Douglas often does, especially around Christmas when the contest season is in full swing.

Elaine Douglas of Beamsville, Ont., with one of the many prizes she wins.
Elaine Douglas of Beamsville, Ont., with one of the many prizes she won. (Elaine Douglas/Instagram)

How does she do this? She has a system. She has an email account — separate from her personal or work accounts — that's just for contest entries, and spreadsheets to keep track of her entries and all the deadlines.

What's more, she's not afraid to put herself out there. 

Douglas recently won a $250 Amazon gift card after entering a contest put on by Veet, which is a product that removes body hair.

"I'm a naturalist. I don't shave. I don't [do], you know, any of that stuff," she said.

But a contest is a contest, even if it required her to film herself shaving. 

"And so I posted a video. It was a minute and 12 seconds, and I had a feeling. I'm like, you know what? There's really low entries on this. Not very many, many people want to talk about how they shave their legs or don't."

According to Instagram, there were only 16 posts with the contest hashtag. Not bad odds.

Know the rules, read the fine print

It also pays — literally, in some cases — to take some time to understand how each contest works, said Michael Wallace, a professor of statistics at the University of Waterloo. 

Wallace figured out a way to game Tim Hortons's Roll Up the Rim contest, and it paid handsomely. All he did was closely read the rules.

These days, the famous sweepstakes for caffeinated Canadians is done online.

Instead of physically rolling up a cup's rim, you get one digital entry for every coffee or donut you buy. You can see whether you've won a prize on the Tim Hortons app or website.

A man poses next to many, many Time Hortons coffee cups.
Statistician Michael Wallace won 94 times out of 96 entries during this year's Roll up the Rim contest at Tim Hortons. (Submitted by Michael Wallace)

What most people don't realize is that whenever people played and didn't win prizes, those prizes went back into the prize pool. 

Wallace saved up his entries until the last day of the contest, and picked a time when he figured few others would be playing.

According to the rules, the odds of winning a draw prize also depend on the number of eligible entries received during the applicable day.

"And at 4:30 in the morning, my phone alarm went off. I woke up, I questioned some of my life choices that had led me to this moment. But I got my phone and bleary eyed, I started tapping away," he said.

By the last day, he'd amassed 96 entries.

"And as I was tapping, I kept winning coffee and donuts and coffees and donuts."

The result? He won 94 times out of 96 entries, although he didn't win any of the bigger prizes.

Meet the contest queen

Carolyn Wilman has won so many sweepstakes that she's earned the moniker "The Contest Queen" among the contest community, and now shares her advice for contest entering with others at contest conventions (yes, that's a thing) and in books and online.

She also advises companies on sweepstakes, and notes it's a way for brands to connect with consumers beyond advertising.

"Let's face it, it's way more fun to create a contest than a plain, boring old ad. And it gets their name out there and it gets their consumers involved with the product."

Toronto brand strategist Gabriella Rackoff agrees. "Contests can work when they add extra value for people who already purchase or would purchase your product," she said.

And although there will always be contest enthusiasts like Wilman and Douglas, "planning contests from a real, happy customer's perspective leads to more sustained growth and retention."

So what does it take to win, again and again?

Like Douglas, Wilman also says the key is being organized. "I tell people: 'Set up an email address just for entering giveaways so it doesn't get mixed in with all your stuff.'" Wilman also recommends using one of several websites that aggregate contests, so it's easier to find them.

After that, it just comes down to putting in the time. And although it sounds like it could be a full-time job, Douglas spends between 45 minutes and two hours a day entering hundreds of contests.

Wilman, who has won dozens of trips to the Caribbean, Europe and Canada, agrees: "People say, 'That's really cool. Can you just tell me how to win?' And they go, 'That's like, way too much work.'

"Listen, when I was lying on a beach in Mexico with my family last October, it [was] definitely not too much work for me."


Adam Killick has been a producer at CBC for more than 20 years, and his work has been featured on almost every CBC national radio current-affairs program. He has won Canada's National Magazine Award for his long-form journalism twice.

Produced by Jennifer Keene.

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