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Canadian contests to enter this fall

3 you can enter for free and 1 with a purchase. I checked the details on 16 October 2026. Sorted by how easy they are to enter.

Free daily habit: enter the radio keywords before 7 pm and make your hockey picks before the first puck drop. Follow @thefreebieladycanada on Instagram for reminders.

Free to enter

No purchase needed · 3

iHeartRadio Big $50K Payday

Free to enterEnds Nov 20, 2026
Win
$50,000 cash, or 1 of 28 prizes of $500
How
Listen to participating iHeartRadio Canada stations for the keywords, then enter them on the contest page at iheartradio.ca. Up to 13 keywords a day, one entry per keyword.
Good to know
Daily cutoff is 7 pm local time. A skill-testing or trivia question applies.
Who
Residents of Ontario, Quebec, Manitoba, Saskatchewan and New Brunswick.
Where
iheartradio.ca → Contests → Big $50K Payday

Tims NHL Hockey Challenge

Free to playEnds End of NHL regular season
Win
Tims Rewards points when your picks score, monthly gift card prizes for the top 5, and a new vehicle plus gift cards for the season's top 5
How
Open the Tim Hortons app on game days and pick up to 3 NHL players you think will score a goal.
Good to know
No purchase needed. Points and leaderboard prizes are shown in the app's Challenge tab.
Who
Canadian residents 13+ (14+ in Quebec) with a Tims Rewards account.
Where
Tim Hortons app → NHL Hockey Challenge

McDonald's Monopoly Golden Edition

Free mail-in optionEnds Nov 2 (codes by Nov 23)
Win
Free food, gift cards, weekly $25,000 cash, $50,000 cash (or 5 million Avion points), McD's for Life, trips and vehicles
How
Each game piece on specially marked packaging has 2 stamps. Enter the codes in the McD's app for instant wins, Collect to Win sets, and Bonus Play. A Bonus Play that doesn't win gives you a Golden Prize Draw entry.
Good to know
Enter codes and claim app prizes by 11:59 pm local time on Nov 23, 2026. Golden Prize Draws are on Dec 10, 2026.
Who
Canadian residents. App play needs a MyMcDonald's Rewards account and age 14+.
Where
McD's app · full rules at mcdpromotion.ca/rules

With a purchase

Receipt needed · 1

Pepsi + Lay's NHL All-Star contest

Purchase + receiptEnds Nov 1, 2026
Win
A 2-night trip for two to the 2027 NHL All-Star Game with flights, hotel and game tickets (valued at about $6,200)
How
Buy a participating Pepsi drink and a Frito-Lay snack, then upload a photo of the receipt at pepsilayshockeycontest.ca. You can enter daily.
Good to know
Check the official rules on the contest site for eligibility and whether there's a no-purchase way to enter.
Who
See the official rules (the site has an age check).
Where
pepsilayshockeycontest.ca

No match. Try another word.

How to get McDonald's Monopoly pieces without buying food

The contest has a free mail-in way to play (no purchase necessary). From the official game details:

  1. Put a self-addressed envelope with enough return postage inside a postage-paid outer envelope.
  2. Write your full return address on the outer envelope and mail it to the address in the official rules (mcdpromotion.ca/rules).
  3. Send each request in its own outer envelope. It must be postmarked by Nov 2, 2026 and received by Nov 9, 2026.
  4. Each valid request gets 2 game pieces (4 stamps), while supplies last.
  5. Enter the codes in the McD's app by Nov 23, 2026, 11:59 pm local time.

Read the official rules before mailing; they have the exact address and any limits per person or household.

Key dates

Soonest first

ContestEndsEntry
Pepsi + Lay's NHL All-Star contestNov 1, 2026Purchase
McDonald's Monopoly Golden EditionNov 2 (codes by Nov 23)Free
iHeartRadio Big $50K PaydayNov 20, 2026Free
Tims NHL Hockey ChallengeEnd of NHL regular seasonFree
Contest safety in Canada

Contest details change, and each contest has its own official rules, which win over anything here. This page isn't sponsored and I don't earn anything from these contests or brands. Brand and contest names belong to their owners; the pictures are drawings, not logos.