WAIPAHU — Sophomore Nick Chang, the seventh shooter for Roosevelt, scored the decisive penalty kick for the Rough Riders yesterday in a dramatic 1-0 double-overtime shootout victory over Castle in the first round of the JN Automotive Group/Hawai'i High School Athletic Association Division I Boys Soccer Championships.

Roosevelt, the O'ahu Interscholastic Association runner-up, improved to 9-6-2 in the regular and postseason and will face No. 2 seed Kamehameha-Maui (14-0-2) in today's 3 p.m. quarterfinal at Waipi'o Peninsula Soccer Stadium.

In other quarterfinal action today at the stadium, it will be No. 1 seed and Interscholastic League of Honolulu champion 'Iolani (9-1-2) vs. Kaiser (11-5) at 1 p.m., No. 3 seed and Big Island Interscholastic Federation champion Kealakehe (15-0) vs. ILH runner-up Kamehameha (9-2-2) at 5 p.m., and No. 4 seed and OIA champ Mililani (13-1-1) vs. 'Aiea (8-5-3) at 7 p.m.

Roosevelt, the OIA runner-up, and OIA No. 6 seed Castle (9-7) had played three times previously this season, with the Rough Riders winning twice.

But yesterday's game was scoreless through 80 minutes of regulation and two 10-minute overtime periods, forcing the penalty-kick shootout.

After the shootout was tied 2-2, each team had an attempt blocked. They then traded goals until Roosevelt sophomore keeper Jay Tsuruoka dived straight to the ground to block the Knights' seventh attempt.

Chang, who had not scored a goal all season, then drilled a shot into the lower left corner of the net to give the Rough Riders the exhausting victory.

"I thought, 'Just get it in,' " said Chang, a halfback. "I thought we had a better chance (in the shootout) because we have such a good keeper."

Tsuruoka participates in the prestigious Olympic Development Program during the offseason.

Castle, meanwhile, lost starting keeper Tyler Esteban to an injury when he was kicked in the head after making a diving save in the eighth minute of the first overtime.

Backup keeper Hendricks Hicks, a sophomore who had not played in front of the net all season, came in and made three saves in overtime and another during the penalty kick shootout.

"That's the first time he had played (goalkeeper) on the field all season," Knights coach Sabo Nakamine said. "He did a good job."

Roosevelt applied a lot of offensive pressure during the two overtime periods, taking two shots in the first 10 minutes and five in the second.

Hicks made a nice save in the 96th minute and a Rough Rider shot a minute later glanced off the front post.

"Castle played well, it's always a battle with those guys," Roosevelt coach Ed Ota said. "For me, I hate to go to penalty kicks because to me, it's a 50/50 chance. We just lucked out."

Tsuruoka made a spectacular save on the Knights' third shot, diving to his left and making a backhanded deflection with his fully extended right hand.

But Hicks matched it with a diving save on the Rough Riders' next shot, blocking an attempt into the lower right corner.

Each team also had near-misses find their way into the net.

Castle's fourth shot hit the left post and then bounced in.

Roosevelt's fifth shot hit the crossbar, bounced straight down and then rolled in.

And the Rough Riders' sixth shot deflected off the top of Hicks' hands and barely squeezed in under the crossbar.

Ota said he did not know what to expect with Chang's attempt.

"In practice, sometimes his shots go high," Ota said. "But today, he did all right."

'AIEA 1, BALDWIN 0

Scott Kawamura scored in the fifth minute and Na Ali'i withstood several shot attempts by the Bears (9-2-2) late in the game.

KAMEHAMEHA 1, MOANALUA 0

Gareth Gomez scored in the 44th minute to lift the Warriors past Na Menehune (7-8-2).

KAISER 2, WAIAKEA 0

Beau Stuber scored in the 22nd minute and Reed Sufrin added a goal in the 49th minute as the Cougars shut out the Warriors (12-4).

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Reach Wes Nakama at wnakama@honoluluadvertiser.com.