Johan Badiuzzaman's escapades in neighbourhoods sometimes ended with disgruntled residents hurling eggs and water bottles - and on one occasion, a glass bottle - at him and his friends.
They were unscathed, but felt misunderstood. To them, they are just a group of passionate skateboarders but they carry the unwanted label of being public nuisances.
The Singaporean hopes to shed this image as the sport prepares to make its debut at this year's SEA Games and the Tokyo Olympics next year.
He is one of the six local skateboarders selected to compete at the Nov 30-Dec 11 Games in the Philippines.
Johan, 27, said: "It's good exposure because right now, in Singapore, people are not really supportive of skateboarding.
"Mostly, out in the streets, if we skate around the neighbourhoods, some people throw bottles and eggs at us. That's a bit harsh.
"If they understand the sport, hopefully they can give us a rest or talk to us nicely."
He and SEA Games-bound compatriot Rocky Chan finished ninth and 10th respectively in last Saturday's Vans Park Series Asia Regionals Championships at East Coast Xtreme Skatepark.
The duo will be competing in the park category at the SEA Games while the other four will be participating in the street division. Unlike the former, where skateboarders perform tricks in giant concrete bowls, street is staged in an open course that has obstacles like rails and stairs.
Skateboarding, which made its way to Singapore in the 1970s, is not a full-time endeavour for Johan, a mechanic, and Chan, a student at the Institute of Technical Education College East.
There is no formal training schedule, but they put in several sessions lasting at least two hours a week after work and school commitments.
Chan, 18, said: "Being alone in the bowl is very demoralising. There's nobody skating in it, we have to feed off our self-motivation to get this far. There's this misconception that people have about us being a nuisance, but they don't see the hard work that we put in."
This makes it a delicate balancing act for the Singapore RollerSports Federation. The national sports association's (NSA) skateboarding section oversees the development of the sport.
It has plans to get certification for coaches, which will provide a pathway for skateboarding to be introduced into schools and expose more people to it.
To prepare for the SEA Games, the NSA is working closely with the athletes to come up with a training programme - a foreign concept for most as they had been largely independent, learning their tricks and flips on their own.
"We are a relatively new NSA in a sport that has been around for so long," said Muhammad Rezal Ramli, the federation's vice-president of skateboarding.
"The sport has already determined its direction, so the difficult part is trying to steer a new, beneficial course that's not against the community's wishes."
But for the scene to grow, local skateboarders feel there needs to be more beginner-friendly facilities.
The $8 million East Coast Xtreme Skatepark, replete with a combo bowl, a vertical bowl and a street course, was launched in 2009 and has earned praise from international athletes like Malaysia's Arina Rahman and America's Lizzie Armanto for being built to international competition standards.
While local skateboarders are appreciative of the facility, they say the course is too advanced, with many struggling to use it. Chan took three years to skate properly in the bowl, and feels it could hinder people from trying to use it because they may be intimidated.
A more diverse facility in Taman Jurong is in the works, but the details of when it will be completed are not out yet.
Despite skateboarding's impending presence at sport's top table, there is a reluctance to move toward the mainstream, especially from those who take pride in the sport's counterculture roots.
"I don't like how the Olympics monetises the sport," said Chan, who has been skateboarding for six years. "Skateboarding is about having fun, expressing yourself and being passionate about the sport. We don't want anyone to start off skateboarding just because they want to make money."