The latest windfall will be delivered with Alibaba's record-setting IPO completed late yesterday, which is expected raise up to $25 billion for the e-commerce company and its early backers.
Alibaba's shares will begin trading for the first time on Friday on the New York Stock Exchange.
Yahoo is in line to make anywhere from $8.3 billion to $9.5 billion from the initial public offering, depending on whether investment bankers exercise their right to buy additional stock in the deal.
The payoff supplements the $7.6 billion jackpot that Yahoo collected two years ago after selling another chunk of its Alibaba holdings and reworked a licensing agreement with the Chinese company.
Even if Yahoo ends up selling its maximum allotment of 140 million shares in the IPO, the Sunnyvale, California, company will still retain a roughly 16 percent stake in Alibaba Group Ltd.
Worth another $26 billion to $27 billion. Not a bad return, considering Yahoo acquired its Alibaba stake for $1 billion in 2005 in a deal engineered by company co-founder Jerry Yang and former CEO Terry Semel.
The Alibaba investment has helped ease the pain of Yahoo's struggles in Internet advertising, the heart of its business. Yahoo's annual revenue has slipped from a peak of $7.2 billion to projected $4.5 billion this year, a decline of nearly 40 per cent.