It's been nine months since Mate Ma'a Tonga's memorable run to the World Cup semi finals, which included a famous victory over New Zealand in Hamilton.
The Kingdom's request for a rematch against the Kiwis in October was rejected by New Zealand Rugby League, who also vetoed Tonga's desire to host the Kangaroos in Auckland.
Woolf said despite both sides wanting the match to go ahead roadblocks keep getting in the way.
"Our first option was that we wanted to play against New Zealand but it was very clear early on that that was not going to happen," he said.
"And as soon as I mentioned it to (Australian coach) Mal Meninga it was something that he jumped at straight away and he's really pushed it and really helped the process along the way.
"You've certainly got two teams that want to play but the other difficulties around it have been particularly to do with finances and who's going to fund it and who's going to underwrite it.
"As well as venues. When it came to New Zealand it's certainly been a bit frustrating."
New Zealand Rugby League expressed concern that a test between Tonga and Australia in Auckland would overshadow their own clash against the Kangaroos at Mount Smart Stadium a week later.
But Woolf disagreed saying matches like these could grow the international game.
"It was very disappointing. I can certainly see the points of view of New Zealand Rugby League but the other thing that I thought was a real positive for everyone was the interest that our game against England (at the World Cup) generated to the New Zealand Rugby League public and the exposure to our game that that gave in New Zealand," Woolf argued.
"Even though it didn't include a New Zealand team I thought it was a real positive for rugby league in the country, therefore I thought it was a positive for us to play over there again regardless of who we were playing."
Australia's National Rugby League (NRL) boss Todd Greenberg was also supportive of the fixture but finding a venue and financial backing was proving to be a major obstacle, Woolf said.
"For a game to go ahead you need support from a local government, you need support from a stadium and it needs to be financially viable," he said.
"And the later that goes obviously that decreases your opportunity to sell it a little bit as well, or to promote it. That, from my understanding, is the biggest hurdle at the moment.
"I have been told through the Queensland Government and through Suncorp Stadium (in Brisbane) there's some interest there and some support there as well but I'm not sure what the actual figures are that are holding up the game."
Cronulla forward Andrew Fifita, who switched allegience from the Kangaroos to represent Mate Ma'a Tonga ahead of last year's World Cup has also voiced his frustration.
Woolf said a decision needed to be made sooner rather than later and he called on the NRL and Rugby League International Federation to step in and underwrite the game.
"I'd be thinking in the next couple of days it certainly needs to be made but it's been a difficult one and a frustrating one," he said.
"There's been a lot of roadblocks put in the way and it's a funny one because everybody that you talk to - whether it be a general fan or people who can act on it - tells you that it's a game that they want to see and a game that everyone wants to happen but everywhere we turn there seems to be roadblocks put up so it's very frustrating."