The season ticket holder sat in the dugout and wore the Spurs manager's gilet during the second half of the club's 3-0 win over Aston Villa at White Hart Lane
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Paulinho opened the scoring before Nathan Baker’s own goal and Emmanuel Adebayor’s penalty put Spurs on course for a comfortable win and a place in next season’s Europa League.
During what is likely to be Sherwood’s final game in charge at White Hart Lane, the Spurs boss invited season ticket holder Danny Grimsdale wear his gilet and sit in the home dugout next to his assistants Les Ferdinand and Steffen Freund.
“It's something that I won't ever forget,” Grimsdale told BBC Radio Five Live.
“To be fair to him, he's not fighting with the fans. He's always happy to chat and have a laugh with us. I called a couple of subs he should make and it just so happened he made them.
“We were 3-0 up at the time and I thought it would be a good chance to bring some youngsters on and he said ‘you know what, why don't you come and have a go’.
“It was just surreal. I didn't know what to make of it, or if I would get in trouble for going over the barrier.
“I’m a lifelong Spurs fan so I'm not going to turn down the chance to sit in the hotseat. As I was walking away he said "you can keep the jacket" and he shook my hand and patted me on the back.
“I don't think he has been treated particularly fairly by the club and sections of the fans. No one in his position would have turned the job down and he has done the best he can do.
“Performances have been more exciting than under the previous manager. But he's a bit of a wideboy and maybe he has just rubbed people up the wrong way.”