The north London side were presented with a fine opportunity to take a top four advantage against the relegation-threatened Cherries, but blew it in devastating circumstances.
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One of Spurs' rivals for Champions League qualification, Newcastle, had lost 3-0 to Aston Villa earlier in the day, and they looked set to be punished when Heung-min Son put Spurs a goal ahead.
However, Bournemouth took a 2-1 lead through Matias Vina and Dominic Solanke, before Dango Ouattara won the match after an Arnaut Danjuma equaliser.
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"It's a shambles," O'Hara said on talkSPORT. "I'm watching this game today and there's no fight, there's no hunger, there's no real determination to win it.
"Newcastle got pumped today, Manchester United have lost Lisandro Martinez, Raphael Varane and Marcus Rashford, Bruno Fernandes gets sent off, all of a sudden it looks like it's going wrong for them - I thought today, 'Spurs could nick this, we can get in there!'
"But did I see anything from Spurs today that warranted being in the top-four? Absolutely no chance!
"Get rid of them! Get rid of the lot of them! I've said it for ages and I keep getting stick from people at Spurs when I say it - get rid of the lot of them. The staff, the players, the dead wood. Start again, rebuild, change the mentality.
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"And if Daniel Levy isn't prepared to change his mentality, he needs to do one as well!"
O'Hara then took aim at the players' mentality, comparing it to his time at the club between 2005 and 2011.
"I am sick to death of watching Spurs every single week and watching the same old rubbish," he continued. "I come on air every week and say the same thing, nothing changes.
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"It's a weak, soft mentality - they're a bunch of losers!
"The team I played in when I was at Tottenham, we weren't Man United and we weren't competing with them, but we were a good team!
"We had winners, people who wanted to win. Alright, we won one trophy, the League Cup, but we were getting there. We had Gareth Bale, Luka Modric, Ledley King, Michael Dawson, Jermain Defoe, Robbie Keane - people who wanted to win every game.
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"They were all at it. Robbie Keane didn't let you have one second off, not even in training, but I look at this team now and I don't see it.
"We've got Harry Kane and he's world class, but I look at the rest of them and think, 'Do you really want to win?' They look like they don't even care!"