Match ends, Middlesbrough 2(2), Crewe Alexandra 2(4).
Crewe Alexandra stunned Middlesbrough as the League Two side beat the Championship outfit 4-2 on penalties in the first round of the Carabao Cup.
Britt Assombalonga missed the target and Crewe goalkeeper Dave Richards saved Marcus Browne's effort in the shootout as David Artell's side caused an upset at the Riverside.
The visitors scored two first-half goals in quick succession through striker Chris Porter and Charlie Kirk as an upset looked on the cards in normal time.
Porter managed to steer in Oliver Lancashire's wayward shot before Owen Dale slipped in winger Kirk to pass the ball into the bottom corner.
But Boro boss Jonathan Woodgate made three substitutions before the hour and his changes paid off as Ashley Fletcher pulled one back with a curled finish.
Debutant full-back Mark Bola then burst through a crowd of Crewe defenders to grab an injury-time equaliser to send the tie to penalties.
Both sides had not faced each other in the League Cup since October 1961, the largest gap between a fixture played in the competition's history.
The win booked a home tie for Crewe against Premier League newcomers Aston Villa in the second round.
Middlesbrough head coach Jonathan Woodgate:
"It was a terrible performance, not what I want from my teams but like I've said before we are thin on the ground.
"I told my players before the game if you don't turn up in any game you'll get done and we didn't deserve to win the game.
"I'll take a couple of pluses from Ashley Fletcher's performance second half, Paddy McNair, Nathan Wood - but apart from that, not good at all.
"We were really sloppy from the start, really, really sloppy. It was a chance for players to stake a claim in the team and they haven't done that."
Crewe Alexandra head coach David Artell:
"I think we deserved to win in 90 minutes. This was a three-quarter empty stadium and it's about mental toughness as much as ability.
"We all want to score, we all want to win, we have technical players, they are not scarred because they are young, it's about believing you are going to score and this was a terrific night's football from the boys.
"They brought the big guns on if you like, even though they already had the big guns on, but it showed how good we were. We deserved to win.
"I have just been told about Villa, I am delighted. It was great reward for a big night's work."
- 8ClaytonSubstituted forMcNairat 45'minutes
- 22SavilleBooked at 60mins
- 14GestedeSubstituted forFletcherat 61'minutes
- 36WalkerSubstituted forAssombalongaat 45'minutes
- 2NgBooked at 68mins
- 5LancashireSubstituted forSass-Daviesat 74'minutes
- 11AinleySubstituted forGreenat 77'minutes
- 16LowerySubstituted forJonesat 82'minutes
- Michael Salisbury
- Shots on Target
Penalty Shootout ends, Middlesbrough 2(2), Crewe Alexandra 2(4).
Penalty saved! Marcus Browne (Middlesbrough) fails to capitalise on this great opportunity, right footed shot saved in the bottom left corner.
Goal! Middlesbrough 2(2), Crewe Alexandra 2(4). James Jones (Crewe Alexandra) converts the penalty with a right footed shot to the centre of the goal.
Goal! Middlesbrough 2(2), Crewe Alexandra 2(3). Patrick McNair (Middlesbrough) converts the penalty with a right footed shot to the top left corner.
Goal! Middlesbrough 2(1), Crewe Alexandra 2(3). Harry Pickering (Crewe Alexandra) converts the penalty with a left footed shot to the bottom right corner.
Goal! Middlesbrough 2(1), Crewe Alexandra 2(2). Ashley Fletcher (Middlesbrough) converts the penalty with a right footed shot to the bottom left corner.
Goal! Middlesbrough 2, Crewe Alexandra 2(2). Paul Green (Crewe Alexandra) converts the penalty with a right footed shot to the bottom right corner.
Penalty missed! Bad penalty by Britt Assombalonga (Middlesbrough) right footed shot is close, but misses to the right. Britt Assombalonga should be disappointed.
Goal! Middlesbrough 2, Crewe Alexandra 2(1). Chris Porter (Crewe Alexandra) converts the penalty with a right footed shot to the bottom right corner.
Penalty Shootout begins Middlesbrough 2, Crewe Alexandra 2.
Second Half ends, Middlesbrough 2, Crewe Alexandra 2.
Foul by Marcus Browne (Middlesbrough).
Perry Ng (Crewe Alexandra) wins a free kick in the defensive half.
Goal! Middlesbrough 2, Crewe Alexandra 2. Marc Bola (Middlesbrough) left footed shot from the left side of the box to the centre of the goal.
Patrick McNair (Middlesbrough) wins a free kick on the left wing.
Foul by James Jones (Crewe Alexandra).
Corner, Middlesbrough. Conceded by Perry Ng.
Attempt blocked. Ashley Fletcher (Middlesbrough) right footed shot from the left side of the box is blocked. Assisted by Britt Assombalonga.
Britt Assombalonga (Middlesbrough) wins a free kick in the attacking half.