Matt Lockwood On Leyton Orient, Dundee And Working For Montserrat

An interview with Matt Lockwood, by Callum McFadden for WFi.

Reflecting on your time at Leyton Orient, which was marked by significant success—including a promotion and multiple selections to the Team of the Year—how do you view your overall experience with the club?

“I had a fantastic time at Leyton Orient, I really did. When I joined at around 20 or 21 years old, I honestly didn’t expect to stay as long as I did. But for one reason or another, I ended up spending nine great years at the club. I played under a very supportive chairman and some quality managers, and ultimately, we achieved success.

“Interestingly, when I first signed for Orient, I had the option to join Neil Warnock at Bury, who were in the Championship at the time. I remember someone telling me that, by the end of the season, both Orient and Bury would be in the same division—that Bury would be relegated and Orient would get promoted from League Two. As it turned out, Bury did get relegated, and we lost in the playoff final, so that prediction almost came true.

“Overall, I thoroughly enjoyed my time at Orient. I performed well for the club, and I felt that the fans really appreciated my contributions during those years.”

As a defender, you scored a fair few goals when during your time at Orient. What do you think was the key to that?

“Well, some might say that defending wasn’t my strongest trait, so I always thought the best form of defence was to attack! After that first season, I ended up taking on penalty duties.

“We reached the playoff final, and during the semi-final, the match went to penalties. Our manager at the time, Tommy Taylor, liked the way I took the decisive penalty and told me, ‘I want you on penalties from now on.’

“Up until then, Dean Smith was our designated penalty taker, and as a traditional centre-half, his approach was just to blast it. It wasn’t exactly scientific—he’d smash it, and nine times out of ten, it would either go in or hit the keeper and bounce away.

“Once I took over penalties, that definitely helped boost my contribution, but as a fullback, I naturally loved getting forward. I had the fitness to overlap all day long, and that really suited my game.

“We used that as a bit of an attacking weapon at Orient, with many of our attacks starting through me. I was fortunate enough to score quite a few goals that way, and I really thrived in that role.”

In terms of your time there, which managers made the biggest impact on you?

“The chairman at the time, Barry Hearn, had a significant impact on my time at Leyton Orient—both positive and, at times, challenging.

“On the one hand, he always looked after me, offering long-term contracts and showing his support. But on the flip side, when bigger clubs showed interest in signing me, Barry often stood in the way, asking for more money than they were willing to pay.

“He’s a great character and was a fantastic chairman, but at the end of the day, he’s also a businessman.

“When one of his star players was performing well, he naturally wanted top money for them, and I can respect that.

“That’s probably a big reason why I stayed at the club for so long—a combination of him valuing me highly and a significant injury I suffered. But I have nothing but admiration for Barry. We still keep in touch, and I see him from time to time. We get on really well.

“In terms of managers, I didn’t work under many during my time there, but the most successful period came under the management of Martin Ling and Dean Smith when we earned promotion.

“Dean, of course, has gone on to have an outstanding managerial career, with stints at Walsall, Brentford, Aston Villa, and now managing Charlotte FC in the U.S. He’s done incredibly well, and it was a privilege to work alongside him during his early days in management.

“Orient is a small club in London, but it has such a tight-knit, community feel. Everyone there contributes so much behind the scenes, and the sense of togetherness was always strong.

“Even after all these years—17 or 18 years since I left—it’s amazing how connected I still feel to the club and the fans.

“When Orient recently came up to Edinburgh to play Hearts, I went out for drinks with some of the fans the night before, and to still be held in such high regard by them is something that means a lot to me.”

After your successful spell at Leyton Orient, you made the move to Nottingham Forest, who were in League One at the time and went on to achieve promotion with them. Looking back, how do you reflect on your time at Forest? Do you feel you would have liked to feature more prominently during your tenure there?

“Absolutely, I would have liked to play more. Unfortunately, I got injured on my debut—the first game of the season against Bournemouth. I went in for a challenge, got hurt, and ended up being sidelined for four months.

“At a club like Forest, that creates opportunities for others, and the player I had been brought in to replace had four months of uninterrupted game time and performed really well. So, when I returned, I found it difficult to get back into the team.

“At that point, I was 31, so I had to consider my future. I only played 11 league games and one cup game, and I had to make a decision—do I stay at Forest and risk playing only a handful of matches, or do I move on?

“In hindsight, I probably should have stayed. At the time, I was the second-choice left-back, but what I didn’t know was that the first-choice left-back would suffer two terrible injuries that season and end up missing a lot of games. I could have had an extended run in the Championship and proven myself to the Forest fans.

“Unfortunately, I wasn’t fully fit, and as a result, I never played anywhere near my best. But that’s football—injuries happen, and there’s not much you can do about it.”

Your time in Scotland with Dundee was unique. Despite financial struggles off the pitch, the club managed to secure promotion to the Scottish Premiership. How do you reflect on your experience in Scottish football, given the challenges and the eventual success on the field?

“The word that best sums it up is crazy. There was never a dull moment during my time at Dundee. Just six weeks after I arrived, the club went into administration, and there was real concern that it might go out of business, with all the players potentially losing their jobs. Shortly after, I was promoted to assistant manager and kept on as one of the 11 players who remained.

“We were then hit with a 25-point deduction, but against all odds, we went on a remarkable 23-game unbeaten run, breaking the club’s all-time record.

“We ended up not only staying up but finishing fifth in the league that season. It was an incredible year—both for the highs and the lows.

“Behind the scenes, watching teammates lose their jobs was tough, but once the dust settled, we knew we had a job to do. The players that were left had a strong spirit, and we fought for each other and for the club, knowing what was at stake.

“That season has come to be known as the ‘Defiant Year’ because we defied all expectations and stayed up. ]

“To this day, when I return to Dundee, the fans still hold that team in high regard. The ovation I received at the Player of the Year event a few years ago was incredible. It was an eventful and unforgettable four years at Dundee, to say the least.”

What did you make of the standard of Scottish football, both in the Championship and Premiership?

“People often ask me about the differences between the standards of football in Scotland and England, and it’s a tough comparison due to the financial disparity.

“In England, the financial resources are significantly higher. For instance, clubs like Wrexham, Stockport, and Notts County in the fifth tier are considered massive by Scottish standards.

“In Scotland, even clubs with significant history like Rangers and Celtic can’t match the financial power of teams like Manchester City or Liverpool.

“If Rangers and Celtic had the same financial backing as Premier League clubs, they could potentially compete at that level. However, their budgets don’t allow them to pay the same wages, so they recruit players accordingly.

“Similarly, clubs like Hibs and Hearts, given their fan base, could be competitive in the English Championship if they had comparable financial resources.

“However, due to the current disparity in wages, English clubs are able to attract and pay for more talented players, which can make it challenging for Scottish teams to compete at the same level.”

With your experience as technical director and manager for Montserrat, do you have aspirations to return to club football as a manager?

“It’s a challenging situation because, ideally, I’d love to pursue a role in club management if the right opportunity arises. The difficulty lies in gaining the necessary experience; you often need experience to land a job, but it’s hard to gain that experience without first securing a role.

“At the moment, I’m thoroughly enjoying my work with Montserrat. We’re focused on improving football both on and off the pitch, and the project is progressing well. So, while I’m open to the possibility of moving into club management in the future, for now, I’m content with my current role and the work we’re doing.”