Tottenham Hotspur suffered an FA Cup loss at the hands of championship club Middlesbrough on Tuesday, losing 1-0 after extra time in the fifth round to Chris Wilder's side at Riverside Stadium.
Josh Coburn scored the deciding goal in the 107th minute as Middlesbrough missed another night after beating Manchester United in the previous round.
It was another blow for Tottenham manager Antonio Conte, who questioned his future after a 1-0 loss to Burnley in the Premier League last week.
Conte fielded in full force, sticking with the starting eleven, which led to a 4-0 win over Leeds United in the league on Saturday, but Middlesbrough was well worth the win.
"This loss hurts me, my players and everyone who works at Tottenham," the Italian said.
"I think we've lost a big opportunity here. When you're playing against a team that's played in the Premier League, you have to hit your opponent as a game.
"You give them confidence when you don't grab the opportunities you've created. They deserved to go to the next round and be praised," he added.
Wilder, whose team is ranked eighth in the championship, credited fans for creating an upbeat atmosphere.
"The supporters gave us the energy to perform at the top," he said.
"We are happy in the next round, I would love it to be a home tie. A big reward for everyone who follows this club."
"We want to make memories. We had one at Old Trafford and I believe we have one at our own stadium, which is fantastic."