NEW YORK — If there is going to be a hockey season, the NHL and the players’ association can’t afford many more days like this.

A long night of bargaining Wednesday that stretched into the early morning hours didn’t end well and likely kept the sides apart for most of the day Thursday. No new full-scale negotiations took place, and outside of a few relatively brief, small sessions on specific topics, it was basically a lost day.

This is now January, and time is limited to reach a deal that would allow for a shortened hockey season. An agreement this week could have led to a 52-game season. That seems all but lost now.

If the sides can’t find common ground within the next week, a 48-game season — the shortest NHL Commissioner Gary Bettman said the league would play — will become impossible, too.

The tenor of the talks appeared to take a downward turn late Wednesday after the players’ association passed on declaring a disclaimer of interest that would have dissolved the union and turned it into a trade association.

The discord carried over to Thursday morning, when Bettman had said he expected to resume negotiations at 10 a.m. at the request of a federal mediator, but the union was holding internal meetings then and didn’t arrive at the league office until a few hours later.