Running the Rails: In a new variation on what was also the first real challenge of the previous season, the drivers each have to drive a Chevy Tracker up a pair of rails, staying on them at all times, then stopping in a marked zone at the end, and then reversing back down them. Unlike the previous season the rails are a continuous slope and do not level off, and this throws Andrew off, nearly causing him to fail his demonstration. Jason takes the challenge first, and almost falls off immediately after failing to adjust his mirrors. After being reminded to adjust them, he gets to the end of the rails without major trouble, but like Andrew he drives too far; unlike Andrew however, he's unable to rescue the situation and falls off the end, failing. Chanie demands that Jeremy do all the thinking for her, and while the two are arguing she drives straight off the end of the rails. Santana fails almost immediately by falling off the rails before she can even get the car fully on them. George's overconfidence and carelessness causes him to fall off about halfway up the track, causing Patrik to deliver on his promise of punching George whenever he fails. Mariah has the best performance so far, getting all the way up the track with no problem at all, but her inattention causes her to fall off when reversing. Tyler becomes another person who fails almost immediately, not even managing to get on the track correctly. Before his run, Ian presents Andrew with a list of his major issues as a driver, none of which appear to be directly relevant to how he actually drives; he subsequently gets all the way up the rails, but drifts so far to the right that he falls off the instant he begins reversing. Siham's confidence issues result in her being incredibly slow while taking the challenge (so slow in fact that Andrew has time to deliver copies of Ian's list to the experts, who question his suitability for rehab if his main issues are things that could easily be addressed without being on the show); she nonetheless becomes the only driver who passes, though it takes her over an hour to do so.
Head-to-Head Reversing: In this challenge, which is being run for only the second time in the show's history (the previous being in Canada's Worst Driver 8), the drivers are split up into two Honda Civic coupes and have to reverse in a straight line down a short course, turn around in a small area at the bottom, and then reverse back up the lane they started in. Santana and Siham are first-up, and while Santana completes the course quickly and flawlessly (so much so that she even has time to complete a second, equally flawless run), Siham refuses to apply the advice to look where she wants to go, and consequently is very slow and causes a lot of damage to the course. Jason and Tyler are second; Tyler gets down the starting lane without too much trouble, but his turns in the bottom part of the course are far too wide, resulting in him knocking down several of the wheel rims that are bordering the course, and this combined with the fact that he holds the steering wheel at the bottom rather than the top causes him to fail. Jason does even worse, and experiences repeated collisions in both directions. Chanie and Mariah make up the third heat, and both fail after experiencing several collisions in both directions, although Chanie is by far the worse of the two, taking more than twice as long as Mariah and causing the most damage to the course yet. George and Ian are the final pairing, and while George passes with no trouble whatsoever, Ian (who again has a "Taxi" sign attached to the roof of his car) has the worst run of the day, veering wildly around the course and causing massive amounts of damage.
Cadillac Challenge: Eye of the Needle: For what is one of the show's most well-known challenges, each driver must drive the Cadillac at a constant 70 km/h, and navigate it through five arches which have been each staggered by the width of a highway lane. Santana is first-up, and a combination of her being taken aback by the Cadillac's power and failing to look where she wants to go results in her hitting two of the first three arches and missing the last two entirely. Tyler does little better, failing to drive the required speed, clipping two of the arches and smashing the final one. Mariah drives far too fast, speeding up to 100 km/h, destroying the third arch and not being able to reach the fourth. Chanie smashes all but one of the arches due to driving too fast (at 90 km/h) and wearing cumbersome wedge shoes. George earns Andrew's ire by mocking the drivers who failed to complete this challenge in previous seasons; subsequently, he gets through the course without hitting anything, but his run is deemed a failure since he took the course at 85 km/h instead of the required 70 km/h. Jason's run is the worst so far, as he drives at 90 km/h and not only smashes three of the arches, but even destroys a camera placed by the side of the course; this, combined with his inability to see Andrew waving a large sign at him from around 50 feet away at the end of his run, causes the experts to seriously question whether Jason should be driving at all. Siham quickly loses her composure after hitting the first arch, and hits two more and misses one. Ian manages to get through most of the arches, but ruins an otherwise-decent run by smashing the third arch.
After the Eye of the Needle, the experts confront Ian about the list he gave them, noting that the issues he listed indicate that he is someone who until now simply wasn't prepared to put in the effort required to be a good driver, rather than suffering from any technical issues; Ian in turn admits that he has decided to give up being a taxi driver, and was only even doing the job to fund the journalism degree that he's currently undertaking. George is the only driver who actively wants to graduate, while the others all admit that they still need a lot of work before they can even consider graduating.
The panel are split, with Andrew and Philippe wanting to graduate George for being technically the most proficient driver, but Cam and Shyamala favouring the notion of graduating Ian, who despite not passing any challenges is clearly not the worst of the group, and has shown awareness of the issues he needs to address; they also feel that George's arrogant attitude and the possibility of him teaching bad habits to his 16 year-old son is a deal-breaker. Tim sides with Cam and Shyamala, and so Ian becomes the first graduate of the season, surprising nearly all the other drivers. Before Ian drives himself home, Andrew makes him remove the "Taxi" sign from his car, and wishes him a successful career in journalism.