Wolves' Bloxwich boy Lee Naylor who went on to face the very best

And the answer has nothing to do with the World Cup, where that first two mentioned have matched into the quarter finals with Argentina and Portugal respectively.

For our purposes, the only acceptable response is that Lee Naylor played against all of them.

Or should that be flipped.

They all played against Lee Naylor.

Not bad for a boy from Bloxwich!

He lined up against Ronaldo whilst at Wolves, but the remaining roll of honour came whilst representing Celtic in the Champions League.

Including one epic night at Parkhead back in 2008 when the Hoops were on the wrong end of a five-goal thriller against a Barcelona team boasting Messi, Henry and Ronaldinho as their front three. With Eto-o and Eidur Gudjohnsen coming off the bench!

And yet, at the time, it wasn’t something the flying left back thought too deeply about.

More so now, when he looks back at such a stellar cast of opposition, it is more worthy of reflecting on, especially if making a ‘pitch’ to potential players in his role as an agent.

But it is certainly something he should be proud of.

“It’s a story to tell when you look back now isn’t it?” Naylor reflects, completely matter-of-fact.

“Especially now I’m an agent – there aren’t many others who can say they went directly up against Ronaldo and Messi!

“I feel fortunate to have done so and played against the very best, but at the time, it probably didn’t massively register with me if I’m honest.

“I had a lot of confidence in myself at that stage, and those days were more about trying to win than who I was up against or getting anyone’s shirt after the game.

“There were some amazing experiences, playing in the Nou Camp, at the San Siro, and that can never be taken away from me.

“But it’s where I felt I should be at that time, it was just me playing football, enjoying it, not thinking I’m a superstar or anything like that.

“Yes, there were some very good opponents, and I loved those sort of challenges, because if you don’t enjoy playing against the very best then you shouldn’t be a footballer.

“And I might bring it out if I’m speaking to a player in my role as an agent, because it’s good experience and something I can pass on.

“But at the same time, that only gets a player interested, and it’s about how I work as an agent, and how I can support them on and off the pitch, that determines how well I do.

“Maybe it can help them on their journey a little bit, but at the end of the day it’s always about the player and what they do, not about me.

“It is a nice story though, but one I have only really thought about more since I stopped playing.”

Naylor’s calm and even blasé assessment will come as no surprise to those who know him as someone who just always loved his football and enjoyed tearing up and down that left flank whatever the challenge and whoever the opposition.

That carefree almost ‘jumpers for goalposts’ approach was exactly the same in his formative years, albeit those were spent playing up front, on home turf, for Forest Star in Bloxwich.

His coach Colin Eaton was then a Wolves scout, and recommended Naylor to the youth ranks at about 10, and despite initially not enjoying it and taking something of a sabbatical, he returned a year or so later. And stayed for a further 16.

Converted from a striker to a left winger, and then, by Robert Kelly, to a left back, Naylor also endured some ‘tough love’ at the time which, with the benefit of hindsight, he realises was crucial.

“I remember going into my first full year of the YTS at 16, Chris Turner, the manager at the time – he was really ‘on me’,” Naylor explains.

“It was the same the second year, all over everything I did, everything I said, all the time in training, and I’ll be honest, at the time I was thinking ‘get off my back’.

“But now, looking back, I realise he was doing it because he saw something in me - he wanted to make sure I got the best out of myself.”

It certainly worked.

Wolves then Club Secretary Richard Skirrow still recalls sitting next to boss Mark McGhee at a reserve match at Molineux when the 17-year-old Naylor was up against a Middlesbrough team including Paul Merson and Paul Gascoigne. The two were impressed, and McGhee acted quickly in securing Naylor’s long-term future.

It proved the start of a week – 25 years ago in October - which then included signing his first professional contract, passing his driving test and making his first team debut. In that order.

“Something in my second year really clicked,” says Naylor.

“I was scoring goals for the youth team and playing well for the reserves, having first played for them when I was 15.

“There was a reserve game against Middlesbrough at Molineux, and I had one of those nights when it all fell together.

“I was hitting diagonals with my right peg – which is normally just for standing on – and had one of those amazing games that you have every now and again.

“I don’t remember all that much from my career - but I remember that!

“Coming off the pitch Paul Merson came up and said, ‘what’s your name kid?’ and told me it was one of the best performances he had ever seen from a left back.

“That left me on cloud nine and a bit starstruck to be honest.

“I came in next morning for a warmdown and was offered a pro contract – Middlesbrough must have had a nibble! – then I went on to pass my driving test and then got my first team debut away at Birmingham, live on Sky.

“Was I nervous? Oh my word, yes. It was my dream, the one thing I’d been working for.

“I’d had tunnel vision, nothing was ever going to stop me being a professional footballer, that was the mindset I had.

“And for the first ten minutes at St Andrew’s, I couldn’t hear a thing.

“Keith Curle was shouting at me and I didn’t have a clue.

“We lost the game 1-0 and I was gutted with the result but from an individual point of view, it was such a positive end to an amazing week when everything just seemed to fall into place.”

From there, even of such tender years, Naylor ‘nailed’ down the left back slot for large parts of the years which followed, through the many ups and downs that spending any length of time as a Wolves player necessitates.

Examples such as an impressive performance in the sensational FA Cup quarter final giant-killing at Leeds, being followed by being left on the bench for the semi-final against Arsenal typified the often-dramatic Molineux rollercoaster ride.

Or more pertinently following up the collective disaster of the 2001/02 season when Wolves were overhauled in the promotion race by West Bromwich Albion, with the sensational response a year later and one of the best days in the clubs’ history courtesy of play-off glory against Sheffield United at the Millennium Stadium.

All these though are experiences which Naylor can now utilise as part of his role as an agent, passing on that knowledge and expertise to those players under his guidance.

“When deciding to become an agent I had that benefit of already knowing what football is like from a player point of view but I needed to learn all about the off-field work that goes with it,” Naylor explains.

“I got to grips with that and now, with having that experience of playing at a decent level, I think it really helps.

“Especially now, with over 5,000 registered agents all battling for players and to do deals, it’s a big challenge.

“But it’s one I really enjoy, that mix of being able to pass on advice which I learned about what to do and what not do, but also the other side of it which I have developed since working as an agent.”

One of the highlights which Naylor can certainly pass on, alongside taking on some of football’s true heavyweights whilst at Celtic, was that play-off final, which marks its 20th anniversary next May.

Following the travails of the previous season, Wolves didn’t find consistent form until the memorable FA Cup win against Newcastle in early January, from where Wolves only lost two of their next 23 league fixtures, including the trio in the play-offs.

Naylor also chipped in with a couple of vital goals, putting Wolves in front enroute to a 4-2 win at Ipswich with a sublime volley, and then a late free kick securing a narrow 2-1 advantage in the first leg of the play off semi-final against Reading.

“I only ever seemed to score decent goals, when I did manage to score,” he laughs.

“That Ipswich one was funny because we’d been awful and, in the dressing room at half time, Dave Jones was digging us out, people were fighting, it was all going off!

“Dave had a proper go at me as well, which I thought was harsh, but I went out with an attitude to try and prove him wrong and scored an absolute ‘worldie’.

“Then in the play-offs Reading had caused us problems and we knew it was going to be a tough game.

“As soon as we had that free kick, I knew in my head what I wanted to do and it came off my foot so sweetly that I knew it was going in.

“That gave us a crucial advantage for the second leg from where we managed to come through and reach the final.

“And the final – wow, what a day. Although I have to say it passed me by a little.

“If you speak to psychologists, they will sometimes say that when you are so massively focused on something, like a big football match, it can end up passing you by.

“That is what happened to me, and I don’t seem to remember much, and it’s only five or six years ago that I actually watched the whole game back for the first time.

“That was when bits started coming back to me, the big man (Matt Murray) saving the penalty and being incredible that day, all those crucial moments.

“We had such an unbelievable dressing room at that time, a really good mix of talent and experience and the likes of myself, Matty and Joleon (Lescott) who were still quite young.

“Building up to the game, and even coming into the stadium on the coach, I just had a feeling that nothing was going to stop us that day – I was convinced we were going to win.

“Even with the disappointments the fans had experienced previously in the play-offs, I think they felt that optimism too, and that was in my head right from the start.

“When we first went out to walk on the pitch ages before kick-off, our fans were already in there, making so much noise, and there were hardly any from Sheffield United.

“That is one of the few things that I have always remembered from that day, just thinking, ‘this is us, no one is beating us today’, and that was how it played out.

“The way we started the game, they just couldn’t live with us, and going in 3-0 up at half time, there aren’t many teams who can come back from that.”

Sheffield United certainly couldn’t, leaving Naylor at the heart of the intense celebrations that heralded the end of a frustratingly painful 19-year absence from the top division and a first ever taste of life in the Premier League.

That was perhaps more of a sobering experience, although, even in relegation, there were more experiences to cling onto with Naylor a league ever-present in his early twenties.

It was an unforgiving arena he always planned and hoped to return to, along with trying to build on England Under-21 honours earned in a team including the likes of John Terry, Michael Carrick and Jermain Defoe, to the progression of a senior Three Lions call-up.

Moving to Celtic at a time when Wolves were undergoing their early transformation under Mick McCarthy was a step up in itself, and a fantastic challenge, but one from which at some stage Naylor had aimed to return back to the English topflight.

“In my early twenties I had felt like something clicked again and I moved up another level,” Naylor remembers.

“I was going through games just not wanting them to finish and couldn’t wait for the next one to come around.

“I remember winning the Player of the Year award (in 2000/01) and was flying, just loving playing football.

“It got to the stage at Wolves that things were changing and I wasn’t too sure where the club was going to go.

“I had been there for 17 years or so and still had the dream of going back to the Premier League and of playing for England.

“Was that going to happen for me playing at Wolves? I didn’t think so.

“Celtic are an absolutely huge football club and going there was an exciting challenge in itself but I also thought it might eventually lead on to coming back to the Premier League, and possibly playing for England.

“I had an amazing first season which ended up in being recognised as one of the Players of the Year in Scotland, the award eventually going to (Shunsuke) Nakamura, who thoroughly deserved it.

“I think the England scouts came to watch me once at Inverness – we never did well at Inverness – and we lost the game and I’m not sure they ever came back.

“I did o-k in the second season as well and ended up staying there for four years and it got to a stage where I turned 30 and knew that the Premier League dream was not going to return.”

There was perhaps one final chance to reach the top tier after being reunited with manager Jones at Cardiff, but the Bluebirds couldn’t press on from a blistering launch to the 2010/11 season and finished up – as so often in that era - losing in the play-offs.

At one point, there was actually a chance of a second stint with Wolves, Naylor returning to train at the club during Dean Saunders’ tenure, but he didn’t quite have the immediate level of fitness to hit the ground running in a way that was required at the time.

He would later make 13 appearances for Accrington Stanley, unpaid, as a favour for their boss and his friend James Beattie, before rounding things off with several outings for Derby County.

In total he made 529 career appearances – 333 of them at Wolves – and scored 14 goals, of which nine came whilst at Molineux.

After hanging up the boots he admitted there were a couple of years of relative inactivity whilst deciding on his next step.

“I played a lot of golf,” he laughs.

Naylor, now 42, had several property interests, which he has maintained, and did complete his UEFA ‘B’ license but ultimately leant towards becoming an agent rather than a coach for an increased sense of job security.

He is also a regular pundit alongside Mikey Burrows and fellow former full back Andy Thompson on Wolves TV – “passing on my expert advice” – and, as befitting his new industry, is always a keen watcher of football whether it is in heading to Molineux or watching the World Cup on television.

And that is where, when watching defenders trying to cope with a perhaps slightly ageing Messi and Ronaldo, Naylor can reflect on the fact that he came up against both when they were properly in their prime.

Although it was always a very different challenge facing those two in comparison to mere mortal opponents!

“Messi and Ronaldo are very different because it’s not like they are out-and-out wingers who you end up marking all game,” he explains.

“They come over to your side to do a bit, and then they’re off somewhere else, and that’s another reason why they are so tough to play against.

“The way they play, their skill, the goals they score, their footballing brains in how they link up with others, they are obviously the elite.

“And at the same time, they are unbelievable athletes as well, which is why they are still going strong and still making an impact after so many years.”

So, the age-old question which continues to permeate football and divide opinion across the globe: ‘Who is the best?’

Naylor laughs.

“That’s the one which is always goes off in my WhatsApp chats – who is the best out of Messi and Ronaldo.

“There have been so many fights and laughs around that question, but it’s all good fun.

“What do I think? I don’t think I can actually say. They are quite different players who have both had incredible careers so I wouldn’t want to separate the two.”

Sitting on the fence, taking a step back, without having to make a decision. Now that’s a luxury Naylor couldn’t afford when lining up against some of those illustrious names during his successful playing career. Those were the days.