The qualifier is called "The Winter Wonderland Qualifier". It consists of many winter-themed and snow-covered obstacles, starting with "Nana’s House" which features a "pie in the face" piston arm, two "French doors" that swing open to hit them, some snowmen, and "Fido" the dog who comes out of his doghouse to trip contestants into the icy muddy water. Next is the classic "Big Balls" with an all new "motivator" called "Snow-tivator", which is a sped-up forward-moving Dreadmill that helps contestants "get motivated" leading up to the big balls. Then there is the "Snow Plow Sweeper", a long sweeper bar that clears a path to the final obstacle, called the "Yule Log Jam", two moving platforms made to look like logs the contestants must cross to get to the finish platform.
- In Episode 2 (Winter Wipeout: The Musical), "Nana's House" was replaced with a new obstacle called "Mogul Madness"--a ski slope that hits contestants (while wearing fake skis) back with moving sweeper arms while their hanging from a crossbar on a zip-line in mid-air.
- In Episode 3 (Don't Fear the Beaver), the first obstacle was called "Winter Wonder Planks", which is the winter version of the standard moving piano key platforms.
- In Episode 4 (Baby, It's Blob Outside), the first obstacle called the "Winter Brr Blob" featured a 1,000 pound bag that dropped on a floating air bag platform that launched contestants 50 feet in the air into the water below. The third obstacle called the "Snowman Sweeper" were a two rotating sweeper arms made to look like snowmen - it is best described by the hosts as "Frosty the Snowman coming back for revenge!"
- In Episode 5 (Hockey Pucks and Bieber Fever), the first obstacle called "Gingerbread House" is a candy coated version of "Nana's House" complete with a gingerbread Fido dog.
- In Episode 6 (This Little Piggy Went to Wipeout), the first obstacle was changed to "Holiday Hams", which features four moving pig platforms that as the hosts say, leaves contestants "glazed and confused".
- In Episode 7 (Some People Just Don't Know When To Quit), the first obstacle is called "Snowman Surprise", which features two snowmen heads on a spinning sweeper arm and a hidden trap platform that surprises the contestant when it swings backwards into their face. The third obstacle's name was changed to "Polar Bear Express", which has the same spinning sweeper arms, only with polar bear heads on the end on them. The hosts stated, "Please don't feed the polar bears...anything but contestants!"
- In Episode 8 of Family Winter Wipeout (Family Night, Kids Eat It For Free), the first obstacle is called the "Snow Blower", which is two rotating wall platforms with three sweeper arms jetting out to trip up the contestants--as the hosts say, "sidewalks and kids beware!" Then its onto the "Icy Balls", which is just the Big Balls with foam on them. Then the continuation of the Polar Bear Express obstacle and Yule Log Jam.
- Round 2
The Ski Lift: Twelve contestants start out on elevated platforms ten feet above the icy water. As this giant ski lift moves in a circular motion, they have to hang onto the handlebars as long as they can, lifting themselves over the frozen sweeper arms to avoid being knocked into the water. Going under the sweeper arm will result in elimination. The sweeper arm will rise higher and higher as they go around. The last six contestants must stay on to advance to the next round and the last one left will win $1,000.
The third round was called "The 7-Letter Word", which consists of seven platforms that spelled the word, WIPEOUT. The contestants will start at the "W" and the first one to the "T" wins. The letters "W" and "I" features sweeper arms, the "P" puddle to avoid, then bounce off the "E" diving board onto the spinning "O" and jump over the three hurdles on the "U" to get to the "T" platform. Contestants who have wiped out after reaching the "P", "E", or the "U" may return to those points instead of starting the entire course over. However, only the best 3 times went on, rather than the usual four.
In episode 4 (Baby It's Blob Outside), The 7-Letter Word featured a person in a polar bear costume scaring contestants on the "P".
In episode 5 (Hockey Pucks and Bieber Fever), the "7-Letter Word" was replaced by another obstacle course called the "Wipeout Ice Arena". For three rounds, contestants start out on the "Dizzy Dummy" a spinning contraption, then they move onto springboards that propel the contestants onto the "Spinning Slap Shot", a horizontal spinning platform trying to make it over the "Penalty Box", a vertically rotating crankshaft. After that, contestants try to avoid being checked by the "Knee Sweeper", a rotating set of connecting bars aimed at their knees, then jumping and spinning their way to the finish platform. While crossing the course, contestants will try to avoid giant hockey pucks being thrown at them by two hockey players (one of them being John Henson) and a female skater.
Round Four - "The Wipeout Zone"
- Bobsled Blastoff
- A mechanical bobsled that launches the contestant out the end of a tunnel into the water below.
- The Icy Stairway from Hell
- An arc of stairs that are lifted up and down from their sides.
- Two slowly rotating platforms with four teethed sweeper arms moving in the opposite direction that the contestant leaps onto.
- Sinister Snowflakes
- Two rotating rigs with 7 spokes that the contestant must cross to finish the course.