Melbourne City's pursuit of Socceroos striker Jamie Maclaren is set to go down to the wire with any hope of a successful move back to the A-League for the Aussie marksman relying on Hibernian's own fortunes in the transfer market.
Maclaren, 25, is halfway through a 12 month loan deal at the Scottish Premiership club - from German second division side SV Darmstadt - but has been the primary target of City throughout January as they attempt to bolster their thin attacking stocks.
The Herald Sun reports that City has less than 12 hours to complete the deal with the A-League transfer window officially closing at midnight tonight (AEDT).
Complicating the deal is Hibernian's reluctance to release Maclaren until they sign a replacement, most likely Reading frontman Marc McNulty, with Hibernian submitting a second offer for the striker after having an initial bid rejected.
Negotiations between City and Hibs are said to have been tense with overnight discussions going into the early hours of this morning (AEDT).
Australia's timezone is set to add another challenge for Warren Joyce's side as the A-League's transfer window ends 11 hours before it does in Europe.
If a deal for Maclaren is to be done, Hibs must complete their signing of McNulty by mid-morning in Scotland to allow City enough time to facilitate all the paperwork between the Scottish side and Maclaren's German parent club.
The former Perth Glory and Brisbane Roar striker is believed to have already agreed to terms with City, but the deal was thrown into limbo after the shock suspension and exit of former Hibs coach Neil Lennon.
The departure of Scottish winger Michael O'Halloran and defender Osama Malik has left City with two vacant roster positions going into the second half of the season.
Brisbane Roar striker Adam Taggart has emerged as a potential back-up option for City if the Maclaren deal falls through, but a shock switch is growing unlikely with such little time left in the transfer window.
An attempt by City to sign Irish striker Wes Hoolahan from West Browmwich Albion has also collapsed, leaving the move for Maclaren the only possible signing for City this transfer window.