The pain of being a Tottenham Hotspur fan has never been summed up better than a miserable night in Croatia back in 2021. Spurs are trying to put past horrors behind them this season and are three games away from doing so in the semi-finals of the Europa League against Bodo/Glimt. 5 Postecoglou is looking to prove everyone wrong with a Europa title Credit: Getty 5 But the competition hasn't always been kind to Spurs Credit: Getty A win in the final would be their first trophy since 2008 and it’s clear manager Ange Postecoglou is all-in having given up on the Premier League. Yet the Europa doesn’t bring great memories for Spurs, particularly as their last shot at the competition in 2021 ended in the ultimate embarrassment. Spurs were midway through their second season under Jose Mourinho who’d been hired as chairman Daniel Levy hit the ‘win at all costs’ panic button. His sophomore season started well and there was even talk of a title charge after a 6-1 win over Manchester United, but as the UK was plunged back into COVID lockdown in the winter, Spurs went back into darkness. Knocked out of the FA Cup at the fifth round stage and with the title gone, there were two avenues for silverware left for Mourinho - the Europa League and Carabao Cup. As spring came round so did the Carabao final at Wembley, and attention was clearly pointed in that direction in Europe. In the last 16 of the Europa, Spurs made the quarter-finals look like a formality thanks to a Harry Kane double in a 2-0 first leg win over Dinamo Zagreb. To put the tie even further in their favour opposition manager Zoran Mamic was staggeringly jailed between the two games. Mamic stepped down immediately from his job three days before the home tie having been handed a four-year prison sentence for fraud. The scales were firmly tipped in Tottenham’s favour, yet over in Croatia, it all went a bit Spursy. 5 Spurs endured a night from hell Credit: Getty 5 There were wild celebrations outside of the ground Credit: Getty Comfortable until the hour mark at 0-0, Mislav Orsic then put the hosts a goal up with a stunning long-range curler before making it two with a crisp finish in the 82nd minute. Mourinho’s side couldn’t respond, and in extra time Orsic completed his hat-trick by tearing through midfield for one of the biggest humiliations for not just Tottenham, but Mourinho too. In an eight minute post-match debrief to the broadcasters, a sullen and stunned Mourinho said: “I don’t need external critics because I feel deeply hurt with what happened with my team. I don’t want to say much more than that.” He did say much more than that, though, and added: “On behalf of my team, in spite of some of them maybe not sharing my feelings and emotions, I can only apologise to the Tottenham supporters. “I’m disappointed with the difference of attitude between one team and the other. “I feel sorry that my team – I belong to that team – is the team that didn’t bring to the game not just the basics of football but, I believe, the basics of life, which is to respect our jobs and to give everything. 5 Mourinho was in disbelief in his post-match interview Credit: TNT Jamie O'Hara names Championship boss he'd love at Tottenham to replace Ange Postecoglou “There was one team that decided to leave everything on the pitch, they left sweat, they left energy, they left blood and at the end they left tears of happiness. They were very humble and very committed. “I prepared my players to play against Orsic, I gave them all the information about him. So I don’t know what else to say.” This wasn’t a Mourinho PR performance either, with captain Hugo Lloris in complete agreement, adding: “It’s just a disgrace. “I hope everyone in the changing room feels completely responsible. It’s a disgrace, what can I say? It’s more than painful.” The result and those around it saw Levy sack Mourinho just over a month later on April 19 a week before the Carabao Cup final against Manchester City at Wembley. Spurs lost that match under caretaker Ryan Mason, and for once Mourinho had been upstaged by his boss - the ultimate humiliation to compound his Croatian nightmare.