Alibaba Group has purchased just shy of 33 million Class A common stock from Nasdaq-listed Groupon.
According to a regulatory filing posted on Friday, the Chinese ecommerce giant paid $101,224,000 for its stake, which equates to just over $3 per share for a reported 5.6 percent holding.
As of close of business on Tuesday, Groupon shares had soared, trading at approximately $4.08 per share on Wednesday morning.
It has not been smooth sailing for the discount site, with the startup going from courting acquisition opportunities from the likes of Google, to suffering in the spotlight since declaring a $750 million initial public offering in 2011.
In October, Groupon's then COO Rich Williams said the company was laying off approximately 1,100 workers in an attempt to restructure and streamline its operations.
Williams also said at the time that Groupon had plans to cease operations in several markets internationally, including Morocco, Panama, The Philippines, Puerto Rico, Taiwan, Thailand, and Uruguay.
Groupon had already bowed out of Turkey and Greece and sold off a controlling stake in Groupon India to Sequoia.
For the 12 months ending December 2015, Groupon posted an operating loss of $79,777, on revenue of $3.1 million.
With revenue of 77 billion yuan for the nine months ending December 31 at hand, Alibaba group has not been light on investments.
On the same day as its Groupon investment, Alibaba purchased 6 million shares from microblogging site Weibo for an approximate $1.1 million, and 740,000 shares in software firm Momo Inc.
Earlier this month, the ecommerce giant led a $793.5 million funding round for augmented reality startup Magic Leap.
The conglomerate also injected $4.63 billion into Chinese retail chain Suning for a 19.99 percent stake; invested $248.88 million for a 10.35 percent stake in Singapore's telecommunications and postal service, SingPost; and in August increased its stake to 66 percent following a $206.45 million investment.
Alibaba pumped $600 million into Travice Inc, the Chinese operator of taxi app Kuaidi Dache in January this year; took a $590 million minority stake in home-grown smartphone manufacturer, Meizu; previously invested $194 million for an undisclosed stake in China Business News; and also sank $118 million into Softbank Robotics Holdings.