I've found that it can depend on the price delta between their price and the matching site's. I've had them match super quickly when the price difference isn't great but when I booked a 10 night stay at a resort in Mexico in March, I had to fight like crazy to get them to price match. I think it took me 8 or 9 emails and a boatload of screenshots before they matched. I was pretty stoked to get a refund of $2,200 so it was well worth the battle.
Koodo $39 / 10 gb