Trailblazer Healy was always in class of her own
How fast should we bowl at her?
Boys from Barker College stressed over this question, as their 16-year-old classmate Alyssa Healy padded up and strolled into the nets.
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Never before had a girl played for the school's first XI cricket team - girls hadn't even participated in the Combined Associated Schools (CAS) competition.
But Barker cricket coaches Steve Thomlinson and Andrew Payne addressed the question before trials.
"I told them to bowl fast," Thomlinson says.
"We spoke about how important it was to have her face the bowling she'd face at CAS first XI, so the boys let loose, but she stood up and batted really well."
Healy impressed the coaches enough to earn a place in Barker's first XI and made history as the first girl to play in the Sydney private schools competition.
Fourteen years later, Thomlinson is still working in the sports department at Barker College and Healy is one of the world's best players, back in Sydney ahead of Thursday night's Women's T20 World Cup semi-final.
Thomlinson remembers Healy's debut for the school like it was yesterday.
"It was against Trinity, we were in somewhat trouble at 7-120," Thomlinson said.
"She went in, first ball, Trinity left hand bowler, bounced her … and she stepped aside and hooked it for four.
"So that was welcome to CAS cricket and the boys … and she'll make it."
But Healy's achievement was not initially celebrated by all - a Barker old boy wrote to the school to express his disappointment that a girl was allowed to play in the CAS competition.
"I suppose it was a big decision, but it was an easy decision," Thomlinson said.
"The guidelines for CAS cricket said that girls were eligible to play … co-coach Andrew Payne and I said she's good enough to play so we played her ... the negative comments were irrelevant to us."
Healy held her own with the boys.
She toured Perth with five Barker cricket teams and played on the school's 2006 CSA championship-winning side.
And to this day, a framed photograph of this old cricket team still hangs up on display in Thomlinson's office.
"Not only was she an actual champion, but with Alyssa in the team, we won the competition," Thomlinson said.
So it wasn't a token that we had a girl, we were the champions,"
"Watching Alyssa play now, you're full of pride knowing she's a Barker girl and that you were involved with her development as a cricketer."
Healy graduated years ago, but Thomlinson believes her legacy rings strong through the school grounds.
"The inspiration of Alyssa comes back to a cricket dinner we had a couple of years ago," Thomlinson said.
"We normally get 140 people, the year she spoke at the dinner we got 240. The junior cohort of the school just love the opportunity to meet with her, get autographs with our own Barker girl who is playing Tests."
After all these years, the former sports master still chats to the Australian wicket keeper and plans to cheer her on at the SCG tomorrow.
"We tweet back and forwards, I give her encouragement from time to time," Thomlinson said.
So what advice does he have for Healy, who has produced both rocks and diamonds with the bat so far this T20 World Cup?
"Form is temporary, class is forever," Thomlinson said.
"And Aussies to win of course."