Back then, they would dream of playing for Spurs in the Champions League.
That dream became reality 15 years later when they appeared as striker and captain respectively in European football’s top competition.
It was a memorable run to the quarter-finals in 2010-11, full of magic moments, moments fans treasure.
Below: Crouchy picks up the matchball after his hat-trick against Young Boys
‘Crouchy’ had a huge influence every step of the way, from getting us into the Champions League in the first place right through to his winner at AC Milan and then the other side of the coin, a red card against Real Madrid at the Bernabeu.
As we prepare for a new chapter in the Champions League and the chance for the class of 2016 to make their mark, we caught up with Crouchy to recall those glory, glory nights.
And it all starts in Manchester…
Below: From The Vault - that win at City in 2009
‘It makes the hairs stand up even now’
Crouchy headed home a dramatic late winner at City on May 5, 2010, to secure fourth in the Premier League and a place in the Champions League play-offs. Cue wild celebrations on and off the pitch…
“It was special. I still remember it fondly. Everywhere I go Spurs fans always come up to me and talk about Manchester City and AC Milan. Those are the two moments.
“City was massive, such a big game and scoring that goal, I don’t think I’ve had too many better feelings to be honest. I’ve had a few, of course, but with it being so close to the fans as well, and being so late on, you could feel the reaction of the fans. It makes the hairs on the back of my neck stand up thinking about it even now.”
Below: Crouchy celebrates his hat-trick against Young Boys
Having reached the play-offs, we faced disaster against Young Boys of Switzerland. Trailing 3-0 in the first leg, goals from Sebastian Bassong and Roman Pavlyuchenko dragged us back into the tie. We finished the job at home as Crouchy’s hat-trick and Jermain Defoe clinched a 4-0 win, 6-3 on aggregate – we were in the group stage!
“I remember the away game. I was on the bench and we let ourselves down a bit. We went 3-0 down! We were bit nervy and we were all thinking ‘we’ve worked so hard to get here and we could go out’.
“There was a lot of pressure on the return leg but everyone was up for it. Thankfully, it was a great moment and a proud night for me. I’ve still got the matchball at home, in the office in amongst my hat-trick balls from my career – but that’s the only one with stars on it! That has pride of place at home.”
Below: Crouchy heads home against Werder Bremen
Our first match in the group stage was a 2-2 draw at Werder Bremen and having scored the goal at City and the hat-trick against Young Boys, who else but Crouchy to score our first goal in the Champions League ‘proper’.
“We’ve Marko Arnautovic here at Stoke and believe it or not, he was at Werder Bremen at that time. He told me that they’d done loads of video work on me in the air and crosses coming in from Bale and van der Vaart and what happened in the first 20 minutes, we scored the header! It was a great moment! We were 2-0 up and should have seen that game out, we ended up 2-2 but it was a good start. Marko laughs about it now. They’d worked on it all week!”
Look out for more of Crouchy's memories ahead of our Champions League matches...