Whitecross ruptured the anterior cruciate ligament in his right knee against Collingwood in last year's qualifying final, requiring a reconstruction.
After a near issue-free recovery, the 23-year-old has spent the past month inching toward full training with skill-based drills and agility work.
He has now progressed to contested and game-based training, taking him a step closer to a comeback.
Listed as three weeks away on the Hawks' official injury list, Whitecross says he is more likely to wait an extra fortnight.
"It's going really well, but there's still a little way to go," Whitecross told AFL.com.au this week.
"I probably could play before the bye, but the doctors and physios have looked at it and said, 'What's the point in playing one game and then having a week off and then playing again?'
"So we'll use the week before and during the bye just to get some extra work in, and look to hit the ground running after that."
While a return with the Box Hill Hawks will be a major step, Whitecross' ultimate goal will be to regain the place in the Hawthorn team he had cemented at the time of his injury.
But the Queenslander is yet to set a target date for that to happen.
"I haven't thought that far ahead," he said.
"Obviously the sooner the better, but at this stage, nine months is a long time without playing, so I'm just keen to get back and play some sort of footy.
"Whether I'm at Box Hill for two or three weeks or six weeks, it doesn't really bother me.
"Just getting back and playing footy is going to be an outstanding result."
Whitecross has been roundly praised for the positive attitude he displayed from the moment he went down against the Magpies, despite the injury coming at the worst possible time.
Forced to sit and watch the 10-point Grand Final loss to the Sydney Swans, his only concern was the team.
"We worked so hard all year long to get there, only to fall short on the day, so that disappointment was greater than the personal disappointment of not being able to play," he said.
"There was nothing I could have done about what happened to my knee, so there was no point feeling down about it."
A short time later, Whitecross also had to overcome another "downer".
He and his dad had been due to fly to Papua New Guinea to hike the famous Kokoda Track the day after the club's post-season best and fairest count.
That trip had to be cancelled – in the short-term at least – in favour of rest and rehabilitation.
"We managed to get a credit [for the cancelled trip], so maybe at the end of this year we'll go, depending on how things go, but certainly in the next couple of years we'd like to go ahead with it," Whitecross said.
Despite the near text-book recovery – many players spend 12 months out of the game after knee reconstructions – the long stint on the sidelines has at times caused frustration.
Always itching to take the next step, sometimes a little too fast, he has had to learn patience as the club's experienced medical and conditioning staff have kept him on track.
The one positive in the whole ordeal has been the reminder about just how much he loves playing the game.
"There's no doubt in my mind that there's a greater hunger there now," Whitecross said.
"It's a positive in a negative, in a way.
"Having that much time out gives you time to sit back and think, and find that appreciation."
