Of all the setbacks during World War II, the one that British Prime Minister Winston Churchill could never really get over was the fall of Singapore. Seventy-five years later, Dara Khosrowshahi shouldn’t even want to contemplate the costs of surrendering the city’s ride-hailing market — for that might mean the beginning of the end of Uber Technologies Inc.’s global empire.

From angry drivers and wary regulators to a sick corporate culture and a founder with outsize voting power, Khosrowshahi, Uber’s new CEO, has a lot on his plate. Add to that the battle for Singapore.

The enemy is Grab, a regional rival that claims to be the No. 1 choice in Singapore, Indonesia, Malaysia, Vietnam, Thailand and the Philippines. On Sunday night, Grab reached out to drivers at ComfortDelGro Corp., Singapore’s largest taxi company, offering them discounts of almost 50 percent on rentals if they switch. Although ComfortDelGro shares fell for a second day on Tuesday, it’s clear who Grab’s real target is: The attack came after the operator said it was talking to Uber about a partnership.

Khosrowshahi is being dared to an all-out war. If he doesn’t take up the gauntlet, it’ll be a repeat of China, where Didi Chuxing forced Uber to throw in the towel.

Singapore is a small market of 5.6 million residents, but 3 million Indonesians came to the island last year to shop and consult with their private bankers and dentists. Add the 1 million visitors from Thailand and Vietnam, and Singapore becomes the beachhead of an emerging single market of more than 600 million. Within the next decade, Malaysia and Singapore will be connected by a 350-kilometer-long high-speed train network. People won’t use different apps at the two ends of their journey. The winner will take all.

But who’ll emerge victorious? Toyota Motor Corp. has invested in both Uber and Grab. The traditional taxi business in Singapore, however, is being forced to choose. Even as ComfortDelGro is thinking of throwing in its lot with Uber, the smaller operators have gone over to Grab’s camp.

Platform markets are double-sided: drivers are as much the customer as the riders. And some innovation, such as Grab’s in-app messaging service that translates seamlessly between Vietnamese and English, can make a big difference to wooing both, as Bloomberg News reporter Yoolim Lee recently found out.

It might appear a small thing, but every little bit counts when the stakes are so high. With Qantas Airways Ltd. ditching the Middle East and returning to Singapore for its Sydney to London flights, Uber can’t afford to be the No. 2 ride-hailing app of choice on the kangaroo route hub. Besides, the anti-Uber alliance cobbled together by SoftBank Group Corp., Grab and Didi includes Ola, which is giving bumper-to-bumper competition to Uber in India.

Losing a second billion-people-plus market to a local incumbent would be a body blow. But if Khosrowshahi can’t win the battle for Singapore, defending the remaining crown jewel of the empire might become that much harder.

©2017 Bloomberg L.P.

This article was written by Andy Mukherjee from Bloomberg and was legally licensed through the NewsCred publisher network. Please direct all licensing questions to [email protected].

Tags: grab, singapore, uber
Photo Credit: Taxis are lined up during a protest against competition from ride-hailing apps such as Uber and Grab at the main business district in Jakarta, Indonesia. Achmad Ibrahim / Associated Press