Late-night scheduling is suddenly the least of Tiley's concerns as the former Tennis Australia supremo contends with player and fan backlash of a different kind.
After 20 years as Australian Open boss, Tiley is presiding over his first US Open after taking on the USTA chief executive role.
He is not Flushing Meadows' tournament director, per se. That title belongs, for now at least, to Eric Butorac.
Make no mistake, though, the ambitious Tiley is already very much hands on, just as he was in transforming the Australian Open into what Roger Federer first famously branded the 'Happy Slam'.
Winning over the players is paramount, which Tiley initially did by swiftly raising US Open prize money to an eye-watering and record $150 million in the biggest single increase in the sport's history.
On site, players are still feted like rock stars by the USTA and will be pampered even more next year upon the unveiling of a luxurious player hub at the refurbished Billie Jean King Tennis Centre.
"As long as I'm happy and the team is happy, then we'll be happy," Tiley told AAP before the Open started.
But Tiley's plans to turn the annual New York major into tennis's new 'Happy Slam' have hit somewhat of a snag as officials strive to strike a balance between sport and entertainment.
One of the chief conundrums centres around who to let in, who can even afford to be let in, and who and what should be kept out.
The rise of social media means 'content creators' are increasingly more important in the corporate world. Having 'influencers' promote brands under New York's bright lights is priceless.
But players are demanding the new-age socialites learn to be seen but not so much heard when grand slam titles are at stake.
"The brands should just educate them on tennis etiquette," superstar home hope and 2023 Open champion Coco Gauff said.
Compatriot and 2024 runner-up Jessica Pegula was less enthusiastic, calling some of the spectator behaviour "disrespectful".
The line between social and traditional media also continues to get blurred. World No.1 Aryna Sabalenka, quizzed by a reporter about her own pre-tournament promotional appearances, was far from thrilled.
"Just because I posted some activities with brands, you think that I've been partying ... think before you say stuff," Sabalenka said.
Spanish young gun Rafael Jodar likewise fumed, having been asked about his shoelaces and perception online.
In the US Open's defence, inane questions are nothing new. Lleyton Hewitt once wanted a reporter from the Nickelodeon magazine removed from his press conference after being asked if he'd ever considered "becoming an astronaut".
But the influx of influencers, who seemingly want to be seen rather than actually watch matches, is becoming a bit much even for tennis's ultimate fashion force Naomi Osaka.
During Osaka's Open opener, a group in a luxury suite at Arthur Ashe Stadium staged a photo shoot that included bright lights while play was underway, prompting the chair umpire to intervene.
The invasion of influencers is also coming at the expense of the traditional tennis fan, who are being priced out.
With bots and organised groups, almost like cartels, dominating ticket pre-sales then posting them online with Ticketmaster at several times face value, fans were asked to fork out as much as $US363.46 for a day-one grounds pass to Flushing Meadows.
That's more than $A500, which won't even get punters into any of the main stadium courts.
The Billie Jean King Tennis Centre being located right next to Corona Park, a vast public parkland in Queens where anyone over 21 is free to smoke marijuana, is also increasing the risk of the season's final slam going to pot.
"Someone is smoking weed," Sabalenka complained to the umpire during her third-round match.
"I was like, 'guys, you can do whatever, you can smoke whatever, you can relax as much as you can. But, please, do not do it around the tennis courts'.
"It's a bit tricky to handle that smell while you're trying to compete at your best."
Veteran Frenchman Adrian Mannarino was less diplomatic about the antics of some spectators, which included crowd chants of "kick him out, kick him out" before a heckler was removed from Louis Armstrong Stadium on Saturday night.
"People are allowed to move around in the crowd during points," Mannarino moaned.
"Before, they were not allowed in the court except during changeovers. Now they come in whenever they feel like it; they move around and talk.
"The tournament puts up with it and I don't know if it's the best thing for tennis in general. There's a smell of marijuana on the court, noise everywhere; the truth is it's turning into a bit of a zoo."
If Craig Tiley's modus operandi is indeed to make the players happy, asking Venus Williams to take the court 13 minutes past midnight on the tournament's opening night may not be his biggest problem.
