IRVING, Texas (AP) — Major League Baseball appeared headed to its first work stoppage in 26 years after a pair of brief negotiating sessions Tuesday led to little or no progress.

The sport’s five-year collective bargaining agreement expires at 11:59 p.m. EST Wednesday, and management is expected to follow with a lockout of the Major League Baseball Players Association.

MLB executive vice president Dan Halem and Bruce Meyer, the union’s senior director collective bargaining and legal, headed talks that took place at the site of the union’s annual executive board meeting. Seven owners also were on hand for two sessions at the hotel, departing the first one to go to their own location after getting a proposal from the union. Dozens of players also were there.

At one point in the afternoon, Halem and Meyer broke off for a smaller meeting that included free agent pitcher Andrew Miller, a member of the union’s eight-man executive subcommittee, and Dick Montfort, the Colorado Rockies CEO who chairs MLB’s labor policy committee.

Players and owners met as a group for a little more than a half-hour later Tuesday.

Major League Baseball hasn’t had a work stoppage since 1994-95. More than a billion dollars worth of contracts have been agreed to in recent days as players and teams try to get deals done in time before a possible signing freeze that a lockout.

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AP Baseball Writer Ronald Blum contributed to this report.

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