Photography by Paul Cooper

Steve Holland

Assistant Manager, Chelsea, 2011-2017

Towards the end of a six-month probation period at Stoke City, I got a phone call from Chelsea.

It was Frank Arnesen. He wanted to ask me if I’d be interested in taking the club’s reserves team, as it was at the time.

It was the summer of 2009, and they wanted me to work closely with Carlo Ancelotti (below) to bring through a group of kids they felt could really evolve and progress. Daniel Sturridge (below), Fabio Borini, Josh McEachran, Patrick van Aanholt… and there were others.

There would be times when these young players would train with the first team, but there would also be times when they’d be playing for the reserves. The club wanted someone who had experience of development but also working with senior players, to see if they could bridge that gap.

Phil Cole/Getty Images

It was a complete contrast to what I had known.

When I was a young player at Derby County, we used to do one session a week in the community programme – we got a couple of extra quid from the club for doing it. The other lads didn’t particularly enjoy it, but I did, so they used to give me their money for taking their sessions every week.

My motivation wasn’t the money, though. I enjoyed it, and then later on I got involved with independent centres of excellence in and around Cheshire – Macclesfield, Wilmslow, Northwich, Trafford. The higher the level of kids I was coaching, the more I enjoyed it.

It was a great place to learn my trade as a coach. Less than 45 minutes from Manchester United, Manchester City, Liverpool, Everton, but if you looked south you had Aston Villa, West Brom, Derby and the other Midlands clubs as well. It was a real hotbed of football.

It was the same during my long spell at Crewe, where all the kids were from one hour away: Liverpool, Manchester, the Midlands.

Ben Hoskins/Getty Images

At Chelsea, things were different. It was a global group: Borini and Jacopo Sala were from Italy, Van Aanholt was Dutch, Gokhan Tore represented Turkey. Daniel Sturridge was English, of course, but he had been at Manchester City for all of his career to that point.

It was a completely different ball game for me as a coach, in terms of understanding the different personalities, the different cultures – of finding a way of communicating with and getting through to players. But it was a challenge I enjoyed, and one that stood me in good stead when I had the opportunity to go and work and with the first team.

Chelsea is an English club playing in the Premier League, but it is very much a European club in respect of the players and the coaching staff usually involved with the first team – and I was lucky to have great interaction with them.

“André was trying to take the team in a different direction, but there was a breaking point”

Every morning I was in the staff meetings, where we would cover the plan for the day, which players would be in which group and what the content needed to be with the players. There were times when I took sessions with Carlo – great experience working with a top-level coach who had very clear ideas on how he wanted his team to play.

Of course, it was a very exciting time at the club. Carlo managed to achieve the double in his first season, and I was around that. I would be in the dressing room at half-time, a privilege I was allowed; I saw how the players behaved, how the coaching staff operated, the communication between them, and of course I got to see the team play up close. It was a great experience, and fantastic for my development.

Despite that, it didn’t feel a natural progression for me to move to work with the first team. I’d managed to have some success with the reserves, winning the national league, and maybe it was just one of those opportunities where you get lucky – being in the right place at the right time.

Paul Gilham/Getty Images

I was actually on holiday with my wife in Spain when I got the call asking me to return. I went back the following day – my wife reminds me of this often – and met with André Villas-Boas (above, centre) and Roberto Di Matteo. André went through what he was looking for and explained his ideas – they were quite different to the direction the team had been going in before. He had just won the treble with Porto and gone unbeaten through the entire Primeira Liga season, though, so he’d had an incredible impact in what was his first year as a coach.

But, of course, Chelsea is a unique club and there were still a lot of senior players around. It was a really challenging season, with André trying to take the team in a different direction; we had results at the start, then we hit a spell where they didn’t come and that became difficult. There was a breaking point, really – the team was changing direction, but if that continued it was likely that the targets we were trying to reach would not be achieved. At that moment, the club made a change.

“Atmospherically, it was the single best night of my eight years at Chelsea”

At big clubs, every day is a drama – but it’s never quite as bad as it’s made out to be. This was a group of players who had been used to a certain direction on the pitch, a certain way of playing that they had success with. If they then get success with a different way, they will buy into the ideas and things will run smoothly; if they don’t, then of course doubts start to creep in.

My job as an assistant had been trying to reassure the players that it was the right pathway, communicating with the manager, acting as a buffer between them and filtering back feedback – in essence, trying to give the whole thing the best chance of working.

Ultimately, it didn’t – but from a selfish point of view it was a good experience to go through. Football isn’t always beautiful. In the end, your ability to handle the bad moments is decisive.

Paul Cooper

There was still a real connection between the players and the supporters though, and that came through in the rest of the season.

We were still in the Champions League, and the second leg against Napoli in the last 16 was, atmospherically, the single best night of my eight years at Chelsea. I have spoken to one or two of the senior players from that time, big players who had experienced a lot at the club, and they felt the same – the best atmosphere there has ever been at the Bridge.

Many of those players had been trying to win what was for them the holy grail for years – and, frankly, time was running out. We had lost the first leg 3-1, and that night we were facing a proper counter-attacking Napoli team with Marek Hamsik, Ezequiel Lavezzi and Edinson Cavani as the front three in a 3-4-3. At that time, they were arguably the most dangerous front three in European football.

“After all the bad luck the club had experienced in the Champions League, maybe, finally, it was Chelsea’s turn”

We were chasing the game, had to commit players forward if we were going to rescue the tie. We needed to score three, so we were going to leave spaces in behind and there was going to be a risk associated with that. But we wanted to prepare the players for that, mentally. If we were to get a negative moment at our end, we didn’t want them to lose heart. All would not be lost.

“Don’t be put off if they get one,” we told them. “We need three anyway, and 3-1 would mean extra-time.”

That’s exactly how it turned out. We got ourselves into a really good position at 2-0; that became 2-1, which doesn’t look quite as good, but we got the third to take it into extra-time.

Michael Regan/Getty Images

It was a night when the big players really stood up not just in terms of goals – Didier Drogba, John Terry and Frank Lampard got the first three – but also in terms of performance. Branislav Ivanovic eventually got the goal that took us into the quarter finals – and maybe that was the point when we started to get a feeling.

Maybe, after all the bad luck the club had experienced in the Champions League – the penalties that hadn’t been given against Barcelona, losing to that last-gasp Andrés Iniesta goal, all those moments against Liverpool – maybe, finally, it was Chelsea’s turn.

We had a magnificent result against Tottenham in the semi finals of the FA Cup, but there was no time to celebrate. On the coach back after the game, we had our laptops out and were studying Barcelona; we had to deliver the gameplan for the first leg of the semi final – we had beaten Benfica in the last eight – the following morning, and the game itself was only two days later.

It was a very tactical encounter, very cagey. We felt Dani Alves would really attack from right-back, so we played Ramires on the left side of midfield. That was different for us, but it worked – Lampard recovered a ball in midfield, played Ramires in behind Alves, and he crossed for Drogba to score. One-nil.

“We were two down and had a men sent off. I looked up at the clock and thought: ‘This is going to be painful’”

The second leg was not tactical.

Roberto Di Matteo, who had taken over from Villas-Boas, used to say to me: “For the first couple of minutes of every game, have a look at the opponents. Let me know what you see, if there’s anything different to what we’ve prepared for.”

After two or three minutes, I remember him turning to me: “What are they playing?”

They had changed, they were playing differently. They were playing a back three, then a diamond, then a front three – which we’d half-expected, but was different. Either way, they had total control of the game – already wave after wave of attack.

“Jesus,” I thought to myself. “Never mind what system they’re playing. I think they’ve got 13 out there!”

David Ramos/Getty Images

By the end of the first half, we were two down and had had a man sent off (above). We’d already made three changes in the back four: Ramires, a midfield player, was at right-back; José Bosingwa, a right-back, was playing centre-back. I’m on the touchline, looking up at the clock, in a stadium of 100,000 fans, thinking: “This is going to be painful.”

Then, just before half-time, we got a counter-attack and Ramires produced a sublime bit of ability to chip the goalkeeper for 2-1. It was huge – it meant we had something we could keep, something to protect.

In the first half, after John had been sent off, we had played 4-4-1 with Drogba alone up front. But we were getting outnumbered in midfield – our two central midfielders couldn’t get any stability at all against Barcelona’s three.

“Drogba was going to be our Lewandowski, and Mata our Kagawa”

So, at half-time, we shifted it. Drogba moved to the left in what was effectively a 4-5-0 and we played with three in central midfield: Raul Meireles, Lampard and John Obi Mikel. It gave us a chance of maintaining a bit of control in that zone, of keeping the ball out of our net – but it also meant that, with no focal point in attack, we had no chance of ever getting out of our half.

But we were set, and for 45 minutes we camped in our penalty area. I know I’m biased, but what followed was, in my opinion, the greatest rearguard action ever by any team in any game.

We had a little bit of luck, the Messi penalty against the bar, and then that incredible moment two minutes into injury time when, for what felt like the first time in the entire second half, my neck turned to the opposite end of the pitch. A white and yellow flash and Fernando Torres (below), all alone, nobody within 30, 40 metres of him.

Only when the ball hit the net did we feel, for the first time across the whole two legs, that we might make the final. It was an incredible moment – one that will stay with me forever.

David Ramos/Getty Images

The Saturday before our last league game of the season, Bayern Munich – our opponents in the final – played Borussia Dortmund in the German Cup final. Robbie and I went to watch, and Dortmund won 5-2. They played 4-4-1-1, with Robert Lewandowski playing in front of Shinji Kagawa and soldiers on the wings to help control Arjen Robben and Franck Ribéry.

We took this from the game, and decided that this would be our way. Drogba was our Lewandowski, Juan Mata would be our Kagawa.

But we had four players – big players – suspended for the final: Meireles, Ramires, Terry and Ivanovic. We had to try and find a way, with the four midfield players we selected, of creating what Dortmund had – a really compact, defensive two banks of four.

“José could dissect how an opponent would play, stop them doing it and find a way to win”

In training we tried Ryan Bertrand, who was a left-back, on the left wing. It looked good. He and Ashley Cole were one in, one out, and we felt it was the best way of controlling Philipp Lahm’s forward runs and Robben’s dangerous positions inside. It’s amazing to think that Ryan would make his Champions League debut in the final, out of position – but he came through, and Drogba obviously managed to get the late equaliser that took the game to extra-time and, ultimately, penalties.

A couple of great saves from Petr Cech, and then Didier was the man to strike the penalty to win us the Champions League. That was very apt, I think, but it was an amazing achievement by an incredible group of players. It was a privilege for me to be involved with them.

Alex Livesey/Getty Images

During my eight years at Chelsea, I had incredible loyalty to all the guys I worked for. I gave everything for every manager I worked with, so it was always a sad moment when changes were made – but this is football, and in the end I came to recognise that my role was to be as helpful as I could to all of the managers I had the responsibility of working with.

That was different across all of the head coaches, really. With Guus Hiddink, I pretty much designed and delivered all of the training; with José Mourinho, he would design and deliver a large percentage – and then, gradually, as I gained his trust, I got more and more to do.

José (below) was fantastic, tactically, at recognising an opponent’s strengths, nullifying those strengths and then counter-balancing that by finding ways to hurt them. I could tell you about so many games where he dissected how an opponent would play, stopped them doing it and found a way to win. Big games, too.

“Carlo could build big respect and get big reactions from the big players – that counts for a lot at a club like Chelsea”

Antonio Conte was different again – not the normal, patient, ‘sit back and wait’ approach we have come to expect of Italian coaches. His offensive play was very structured; we used to train repetitive drills every day on offensive play, not defensive, with an emphasis on getting the ball forwards quickly and tactically with numerical superiorities.

Rafa Benítez was much more reserved: wait, wait, two central midfielders, hard-working wingers, wait, recover the ball and forward, forward, quickly forward. Visualise Steven Gerrard receiving to feet at Liverpool, then into Torres to score – he employed the exact same attacking dynamic at Chelsea.

Then there was Carlo, who was really good on the man-management side too; he was particularly good at building big respect and getting big reactions from the big players, which counts for a lot at a club like Chelsea.

Clive Mason/Getty Images

When I look back now, it looks like I was always the one who was going to stay as the managers changed. But that’s not how it felt at the time, and the stability that I ultimately offered the club came as a consequence of going back to the beginning of a relationship with every new manager who arrived – and really working at whatever each manager wanted and needed me to be.

That was a challenge, a real challenge, and it certainly wasn’t the vision I had of my role when I first arrived at Chelsea.

But it ended up being the role I played – and I reflect on it with a large sense of pride.

Steve Holland


Steve Holland: Part 1

From his time as Chelsea’s assistant manager, Steve Holland revisits an iconic Champions League win over the Barcelona of Lionel Messi and Pep Guardiola

Steve Holland: Part 2

Chelsea, Manchester City and Liverpool have all produced teams that employ variations of the same attacking principles, as England’s Steve Holland explains

England analysis: Positives to Euro 2020 delay

England and Gareth Southgate have an extra 12 months to prepare after Euro 2020 was delayed. We assess what that means for their prospects