The former Tottenham star, who also played for Wolves, Portsmouth, Fulham and Blackpool in the top flight, was discussing his experiences following reports from Chelsea.
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It was claimed that Todd Boehly entered the Chelsea dressing room and called the players 'embarrassing' following Chelsea's 2-1 defeat to Brighton at the weekend.
While he didn't interrupt caretaker boss Frank Lampard and waited until he had finished his own team talk, the idea of an owner entering the changing room is frowned upon.
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Having played in the Premier League for a number of years, O'Hara says that it's no surprise to hear that an owner has entered a manager's territory, telling the tale of particularly memorable time that it happened in his career.
Speaking on The Sports Bar, O'Hara said: "It's happened in the past. It happens a lot.
"I remember a moment when the owner came in and our manager - I won't say any names because I don't want to stitch him up - but the manager was doing a team talk and the owner came in.
"It's the most uncomfortable thing ever and he told the manager to sit down.
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"In the Premier League, he told the manager to sit down and the owner took the team talk for the game.
"He said, 'Look, it's really windy that way so have lots of shots'. I was like, 'What am I hearing?'
"It's so disrespectful and I just think that an owner shouldn't go in a dressing room."
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Jason Cundy also added: "I've had it done. I've had it done when things have gone well and when things didn't go well and you're sitting there and its cringe. It's not pleasant."