Walmart Inc on Wednesday announced it was paying $16 billion for a roughly 77 percent stake in Indian online marketplace Flipkart, the U.S. retailer's biggest deal as it battles rival Amazon.com Inc in a burgeoning e-commerce market. The deal is also Walmart's biggest bet in foreign markets, where it has historically struggled. The retailer's previous biggest acquisition, Asda - which it bought in 1999, was sold last month to Sainsbury's. Deals and investments made by Walmart in the past two decades: Walmart bought UK grocery chain Asda Group PLC in 1999 for 6.7 billion pounds, which was the retailer's biggest acquisition up until the Flipkart deal. Last month, Sainsbury's bought Asda for around 7.3 billion pounds, after Walmart struggled with the business over the past five years. Walmart sold its German retail business to Metro AG in 2006, taking a loss of $1 billion. The terms of the agreement were not disclosed. In 2006, Walmart sold its South Korean retail business to Shinsegae Co for 825 won billion ($882 million). Walmart spent up to 100 billion yen ($878 million) to buy out minority shareholders in Japanese supermarket unit Seiyu Ltd in 2007. In 2012, Walmart got the go-ahead from a South African court for its $2.4 billion acquisition of retailer Massmart In 2015, a unit of conglomerate China Resources Corp plans to sell minority stakes it holds in 21 Wal-Mart Stores Inc outlets around China for $525 million. In June 2016, Walmart sold its Chinese online grocery store, Yihaodian, in return for a stake in the country's no. 2 e-commerce firm JD.com Inc. Walmart paid $3.3 billion for internet retailer Jet.com and its innovative pricing software in the August of 2016. Walmart in January 2017, announced that it was buying online shoe seller Shoebuy.com from Barry Diller's. Walmart bought online outdoor retailer Moosejaw in February 2017 for about $51 million in cash giving the U.S. retailer a slew of popular brands including Patagonia and North Face. In March 2017, Walmart bought women's vintage-inspired retailer Modcloth.com. The value of the transaction was not disclosed. In June of 2017, Walmart said it would buy online men's fashion retailer Bonobos Inc for $310 million.