Shareholders in Australia's APN News and Media rejected a A$3 billion (US$2.5 billion) takeover offer from Tony O'Reilly's Independent News and Media (INM)on Friday.
APN said 51% of the shareholders voted for the deal while 49% against, which meant it fell short of the required number of votes for the A$6.20-per-share deal, by a consortium including INM and private equity, to succeed.
APN said about 80% of its shareholders by number supported the deal, with 24 institutions voting yes, while nine voted no.
APN Deputy Chairman Ted Harris said the deal would have gone through if fund manager Perpetual had voted in favor.
Perpetual, APN's second-largest shareholder, said earlier in the week it would vote against the offer, sending APN's shares lower.
Dublin-based INM and private equity partners Carlyle Group and Providence Equity Partners (PEP) last month upped their offer for APN after key shareholders, including Perpetual, criticized an earlier offer.
APN will meet on Monday to make a decision on dividends for the current fiscal year.
The offer cannot be raised again under Australian takeover laws because it has been declared final.
The deal needed 75% of eligible shareholder votes to succeed. Independent could not vote on its 42% stake.
The failure marks the latest in a string of Australian takeover offers to encounter stiff shareholder resistance, including failed high profile bids for Flight Centre and Qantas Airways.
O'Reilly, a former international rugby player, is Ireland's best-known businessman. "We are going to look at all our options, we are in no hurry to do anything at this point," INM's chief operating officer Gavin O'Reilly told reporters after the vote, adding the setback would not affect INM's Asian expansion plans.