Nick Montgomery enjoyed a fairytale finale in his job as assistant manager at Tottenham Hotspur as he saw the London club end a 17-year trophy drought with victory in the UEFA Europa League final against Manchester United.
Montgomery was recently in Malta and sat down with Gianluca Lia to discuss his experience of being the right-hand man of former manager Ange Postecoglou at the English Premier League side.
Nick Montgomery has enjoyed a footballing journey that took him to several continents, experienced different championships, and has also rewarded him with silverware at one of England’s biggest clubs.
Montgomery carved out a strong career as a defensive midfielder, most notably with Sheffield United, where he made 398 appearances over 12 seasons.
He also had a brief stint at Millwall before heading to Australia in 2012 to join Central Coast Mariners.
There, Montgomery became captain in 2015 and later transitioned into coaching, eventually guiding the club to an A-League championship in 2023. His work didn’t go unnoticed – he was appointed Hibernian manager later that year, although his tenure lasted just eight months.
His link with Tottenham began through Ange Postecoglou.
“When I went to Australia, Ange was at Brisbane Roar, and we faced each other a few times. We always kept in touch. Later, while he was succeeding in Japan and Scotland, I was also coaching in the A-League and then at Hibernian,” Montgomery said.
“When one of his assistants left Spurs, Ange reached out. Within 24 hours, I accepted the role. It’s been amazing to work with him and be part of such a massive club.”
That first season wasn’t without its challenges. Tottenham endured an injury crisis, with key players like James Maddison, Dejan Kulusevski, and Lucas Bergvall missing the final stages of the season. Yet Montgomery praised the squad’s resilience: “We had a short squad, and that’s tough when you’re playing in both the Premier League and Europe. Some of our youngsters like Archie Gray and Bergvall had their baptism of fire but really stepped up.”
The highlight of the campaign was undoubtedly the Europa League triumph – a 1-0 win over Manchester United in Bilbao, with Brennan Johnson scoring the winner.
“It was a remarkable achievement,” Montgomery said. “After such a difficult season, to win a European trophy meant so much. Ending the trophy drought for this club – it was special for everyone involved.”
Balancing Thursday night European fixtures with Sunday league matches proved demanding.
“You arrive home from away trips at 3am, and we didn’t have the luxury to rotate like bigger squads do. Recovery and player attitude were key,” he said.
Montgomery also acknowledged the learning curve: “Tottenham is a huge club with massive expectations. There’s more pressure, more responsibility – you have to be at your best every day.”
The Spurs fanbase, he added, played a vital role: “They’ve been fantastic. To see their wild celebrations after the final – that was unforgettable.”
He also credited Postecoglou’s influence in challenging perceptions. “Ange has been a trailblazer. He’s shown that foreign coaches – especially those from Australia – can succeed in Europe. He’s changed how people view Australian football.”
Montgomery, who spent time in Malta during the off-season, spoke warmly about the island.
“I love Malta. I’ve been over ten times — first came here with Sheffield United when we were sponsored by Visit Malta,” he said.
“I caught up with old memories, including a message I sent Kyle Walker about a trip we took here. It’s a beautiful place, and I know Anton Tagliaferro of Balzan, who is a fantastic person and a great advocate for Maltese football.”