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Trafalgar--$10,000 of travel for 10 Years Contest
Enter for a chance to win $100,000 ($10,000 per year) with Trafalgar Tours that can be used toward any eligible Trafalgar, Costsaver or Brendan Vacations tour. You can enter by attending one of their online travel events, signing up for the newsletter or for Canadians only by mail.
Restrictions:  Age of Majority--no QC--international
End Date: September 30, 2021posted on February 18, 2021
Thanks to: Leecha13 for telling me about this one
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Chrysler--Win Your Wheels Contest
Enter for a chance to win a voucher worth up to $70,000 for a Chrysler, Dodge, Jeep or Ram vehicle of your choice.
Restrictions:  Age of Majority
End Date: December 31, 2021posted on January 14, 2021
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Parent Life Network--Canada's Luckiest Family Contest
Enter for a chance to win 1 of 17 various prize packages that includes $5,000 from Sun Life with groceries for a year, two smartphones, $5,000 for a family road trip or more. The rules are here.
End Date: July 31, 2021posted on February 22, 2021
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Wyndham Vacation Resorts--Chance Of A Lifetime Sweepstakes
Enter for a chance to win a vehicle of your choice worth up to $50,000 or you can take $25,000 in cash. Wyndham Vacation Resorts sells timeshare vacation properties and they may contact you with a sales pitch.
Restrictions:  18 or older--in Canada it's open to AB, BC and ON only
End Date: June 30, 2021posted on January 9, 2020
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Maclin Ford--Ford Bronco Giveaway
Enter for a chance to win a Ford Bronco worth $49,989.
Restrictions:  18 or older--AB only--you must have a driver's license
End Date: June 30, 2021posted on May 10, 2021
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General Motors--Match & Win Contest
Enter for a chance to win your choice of a Chevrolet, Buick, GMC or Cadillac vehicle worth up to $47,000.
Restrictions:  Age of Majority
End Date: December 31, 2021posted on March 27, 2021
Thanks to: JillieN for telling me about this one
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GoodGuys--1967 Chevrolet Nova Giveaway
Enter for a chance to win a 1967 Chevrolet Nova valued at $40,000.
Restrictions:  18 or older
End Date: June 1, 2021posted on October 18, 2020
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Cyberlandr--Win A Truck Camper Sweepstakes
Enter for a chance to win a CyberLandr Cybertruck camper, worth $39,995.
Restrictions:  21 or older
End Date: August 31, 2021posted on April 7, 2021
Thanks to: Hankenstein for telling me about this one
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Vancouver Canucks--Toyota Corolla Contest
Enter for a chance to win a $32,600 Toyota Corolla.
Restrictions:  18 or older--BC only
End Date: May 16, 2021posted on April 18, 2021
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Ford--Built For Adventure Contest
Enter for a chance to win $30,000 to be applied towards a purchase/lease of a new 2020-2021 Ford vehicle. Watch one of the three videos for the contest code--can watch all three for three entries.
Restrictions:  Age of Majority
End Date: June 10, 2021posted on May 9, 2021
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