When tackling any interview, you always worry about whether your guest will be friendly and open or if it will be like drawing blood from stone. Ten minutes in and we had done nothing more than ask about how we were both coping during the global pandemic, checking in on each other’s families and general wellbeing – I had nothing to worry about. What became evident over the next couple of hours was that Seán Dillon is friendly, focused and above all else, an absolute gentleman.
When did you first decide you wanted to pursue a life in football?
I didn’t actually play for a football team until I was about nine. There’s a few different leagues in Ireland and I moved to the Dublin District Schoolboy League – the DDSL, that was the big league at the time. The team I signed for was called Cherry Orchard. I had a couple of trials and spoke with a couple of clubs. I went away to Peterborough, I had a trial at Man City and then I ended up going away to Aston Villa for a trial and that was me. I had a couple of weeks over there and I decided to sign. I must have been 15 then.
What was the transition like, going from your hometown to moving away to a different city, different country?
I was excited about it. Nervous, but excited. I moved in with an elderly couple in Birmingham, in the digs there was three other boys, a couple of English lads and a boy from Sweden. I didn’t really have a lot of time to think about missing anybody: you’re up early, into training, doing jobs, quick shower then back out in the afternoon doing what you need to do. I loved my time at Villa. It was just an amazing time going to play at Villa Park every second week. I missed home, it was tough at times, being on your own. Saturday evening up until Monday morning was probably the worst, being on your own all-day Sunday. I loved it though, I definitely felt very lucky and privileged to be in that position.
Once your time at Aston Villa came to an end you ended up signing for Longford Town, back in Ireland. How did this come about?
I was told around the end of January 2002 that I wasn’t going to be getting a new contract. The club were very good with me. I ended up staying until the end of April, continuing to train with them. I went to the exit trials put on by the FA and got a letter back from the FA with a number of clubs that were showing interest: Bournemouth, Sheffield Wednesday, Oldham and Kidderminster. The collapse of ITV digital meant that a lot of teams had to pull out and kyboshed my chances of staying in England at the time.
I had one night with Shamrock Rovers – I really enjoyed that. Noel Hunt was there. I didn’t know Hunty at the time but he was very good, looked after me a lot. I then met with Longford Town, they made me a really good offer. I agreed the deal with Longford and signed on the Monday evening. On the Wednesday evening the manager turned up and said goodbye to everybody – he’d just been sacked! On the Friday night the league started and I played my first game.
What was that debut like?
I don’t remember, I got a concussion during the game! I finished the game and it was only after that I was told I wasn’t making any sense. I remember walking into the stadium and that’s it. The next thing I remember is waking up at home on Saturday morning, still in my kit. My ma had to explain to me that I’d played the game and I’d been at the hospital most of the evening before they let me go home to sleep it off.
After a couple of years at Longford you moved on to Shelbourne in 2006, staying for only one season. What happened there?
I loved my time at Longford but I decided I wanted to have another go at full time football. I signed for Shelbourne around Christmas, 2005, signing a three-year contract. 2006 was the best. It was an amazing time, playing for a Dublin team in Dublin, winning the majority of our games. We won the league on the last day. Craig Levein had come over to watch that game. I’m not sure exactly who he had come over to see, I’m not going to say he had come over to see me specifically. There had been trouble throughout the whole year with regard to wages. We had been getting paid late and there was a bit of trouble. We won the league on the last day of the season and then I went about seven weeks without money. That’s how my move to Dundee United came about really, I don’t think I would have got the move if everything was fine.
How exactly did the move to Dundee United come about? Was there any competition for your signature?
I spoke to Craig [Levein], Houstie [Peter Houston] and the old chairman, Eddie Thompson, who was amazing when we met him. The PFA in Ireland were helping me recoup the money that I was due and in fairness to Shelbourne, I was paid every penny. Craig said all the right things really; that he didn’t want to wait another week or two to see what the tribunals said, it wouldn’t cost much money and they were willing to pay that. That to me just confirmed everything I felt about the move. Steven Kenny was the Dunfermline manager at the time and he was wanting to meet with me during my trip to Scotland. I spoke to my uncle in Glasgow, a massive Celtic fan who told me, ‘Look, Dundee United are a really, really big club, Seán. I’m not knocking Dunfermline, but if you’re asking me what my opinion would be then it’s them.’
You spent your season with Shelbourne winning game after game on your way to the title, what was it like transitioning from a winning team to one that was fighting a relegation battle?
When I signed for Shelbourne, Pat Fenlon made it very clear that if we don’t win the league, we had failed. I had an idea what was going on when I signed for United, it was a bit scrappy but you got the impression that there were new faces coming in and that it was a case of getting over the line really and being safe. To be honest I was just on such a buzz – I was playing in the Scottish Premier League! I was just focused on making myself better. I had Barry Robson playing in front of me and Lee Wilkie beside me at the back. Willo [Flood] then arrived in the summer and you were just desperate to impress. We made sure that we survived, which thankfully we did, and then obviously looked forward to next season and starting fresh.
Your debut was a 5-0 defeat at Ibrox. What was going through your head that day? Was it just a bad day at the office or were you worried you were in over your head?
I think it was Walter Smith’s first game back in charge of Rangers. Even though we got beat 5-0, it was still my debut, it was just mad. I’ll never forget walking down the tunnel at Ibrox. When the tunnel is pushed out you don’t actually see much until you get right to the end of it. You kind of see the pitch, the music changes and the crowd know then that the teams are coming out. It was nuts. I remember Levein having a go at Garry Kenneth and I just thought ‘Jesus man’, not that I needed any more motivation, but I certainly didn’t want to be on the wrong side of that.
You’ve already mentioned two sides to Levein, the warm, welcoming guy and the more aggressive ‘hairdryer treatment’ type. What was he like as a manager?
He’s the best manager I’ve worked under. I’ve been very lucky to work under a lot of really good managers but he just made things really simple to understand. He had a passion, an aggression. There was a fear factor there, no doubt about that. If you made a mistake trying to do the right thing then Craig wouldn’t have any issue with that. He’d rather you dribble and try and hold the ball up and then make a pass when one becomes available, rather than just clearing the ball. You wouldn’t dare be lazy, and if you were doing stuff that hadn’t been asked of you to the detriment of the team then you didn’t get away with it. He was brilliant though. He definitely had a toughness in him, a strictness, a professionalism, he just wanted things done right. I’ve met him a few times since he’s left and I still feel the need to call him gaffer!
Your first season was about fighting off relegation, the year after saw a real turn around as the team reached the CIS Cup Final against Rangers. You played so many games that season but didn’t play the cup final… why?
Although I still say Craig is the best manager I’ve worked under, you don’t agree on everything. I’m almost certain Mihael [Kovacevic] made his debut at Parkhead on the Wednesday before the cup final. He was playing right back up against Aiden McGeady and done really well against him. I think we drew 0-0. There was a number of lads left out the squad or on the bench, who we presumed were just being rested. Craig named his team the day before the game, just before we trained, and that was it, we didn’t speak about it one to one.
After the game Eddie Thompson came into the dressing room and went around every single player, shaking our hands and basically saying unlucky, telling them how great they played. He apologised to me for not playing. He was really ill at the time, I couldn’t believe it that he was going around, doing and saying those things to people in the condition he was in. He was brilliant, really, really good with us. As much as I was annoyed, upset, angry about the game, the bigger picture was that this man was dying. It meant so much to him and unfortunately on the day we just couldn’t deliver the trophy for him. It certainly would’ve been a magic moment for him and his family. My personal feeling went out the window when he walked in and did that.
Mark Kerr played over 150 games for United but is remembered by so many for one mistake, his backpass in that final. What did you make of that?
That’s football, that’s the way it is. Don’t get me wrong, I’m not knocking anyone for doing that. You look at how that game panned out, should we have scored more goals? Probably, yeah. Should we have conceded the other goal? No. Does anyone remember how the other goals were scored? Does anybody remember who missed the penalties that day? Should Łukasz [Załuska] have saved any more penalties than he did? You know, you have all these different things that are part of us losing that game, but the goal that Kerzo gave away wasn’t the winning goal. We didn’t even lose the game, that’s the other thing. It took penalties for the result to be done. I’ve no problem with people having opinions. I just try to be positive. When you mention Kerzo’s name, that’s not even close to what I’d be thinking. He’s one of the guys I look out for and am delighted to see him doing well in the role that he has at the moment.
The 2010 Scottish Cup final probably has a few more happy memories attached to it. That run to the final all started away at Partick in January. It began with a controversial goal from Damián Casalinuovo, the ball bouncing off his hand and in.
Bounced off his hand? That’s putting it nicely! It’s hard to believe that it wasn’t seen. We were warming up by the corner flag, the lino was on that side, standing right in front of the crosser… I don’t know how it was given. I don’t know how he got away with it, but he did, thankfully, and Goodie [David Goodwillie] managed to score at the end to see us over the line.
You had a game at Ibrox in the cup, a game which saw some atrocious referring decisions, but dug deep and earned a replay at Tannadice where David Robertson managed to score a late goal with his backside. I don’t recall hearing a noise like that at Tannadice before. What was it like being on the pitch when that went in?
It was nuts! To go from where we were at Ibrox, you’re thinking certainly having done the hard work there’s still a long way to go. Kris Boyd came on just after Robbo had scored. I knew enough about the recent history to know that Kris Boyd’s scoring record against United was a joke, so to see him coming on the pitch you’re just thinking ‘oh no, you’re the last person I want to see’. It was nuts when Robbo scored the goal and then the celebration afterwards was brilliant like.
Were you happy with Raith in the semi-finals?
The semi-final weekend was the big one for me. We trained on Saturday morning, Celtic played Saturday, early kick off against Ross County, so we were getting on the bus as that match was finishing so we knew that we were travelling down to Hampden to play a Division 1 team, knowing that we had another Division 1 team in Ross County if we won. We took nothing for granted and the Celtic result was an eye opener, definitely a big warning for anyone that thought it was going to be an easy ride, and it certainly wasn’t. Houstie did a fantastic job of keeping us all grounded.
Ross County in the final. What was your standout moment from that day?
Travelling on the bus to the stadium, seeing all the fans, that’s always a good buzz. You get all your gear on, go out on the pitch, all that stuff is great. I was lucky enough to have won a couple of trophies back home, but the league win with Shelbourne, we won on the last day and we won 2-1… we were really holding on. We won the cup with Longford, again 2-1. We had a 2-0 win in a final, but scored the second with the last kick of the game.
The reason I’m saying all this is that the standout for the Scottish Cup was Conway’s third goal because when that one went in there was definitely no coming back. It is hard, it can be difficult to really relax and enjoy it when there’s so much at stake, and that’s even for your normal Saturday three o’clock kick offs. So when you’re going out for a cup final and competing for a trophy that the club has only won once before, it’s incredible. You think about the great history of the club and the amazing times that the club have had and it’s only five top flight trophies: one Premier League, two cups and two league cups.
Our last victory was in 1994, and it has already been a decade since we won in 2010. To have started the cup final means that you will never be forgotten at Tannadice.
I probably won’t really appreciate it until I’m actually finished and I’m looking back at it. It is nice to be part of that though. I would never consider myself to be in the same bracket as the likes of Eamon Bannon, Hamish, Heggie, Paul Sturrock… I would never, ever consider myself remotely close to them guys, but when you look back and you’ve been part of one special achievement for the club, it is a nice feeling.
After years of playing the same teams over and over again in the league, what was it like getting to play competitive European football?
Night-time games are great anyway, but when you’re involved in the European games it’s brilliant; there’s just such a buzz about the place. Getting to travel to those places, being involved in the games – just really, really good. We didn’t have great success, unfortunately. That first year with United, we knew we only had to get through that one game to qualify for the groups and unfortunately, we were just a little bit shy.
In the years following that 2010 cup final we started to see a lot of key players leaving, going down south. Was there ever any interest in yourself; did you have any desire to move away, or were you firmly settled at Tannadice?
I was fairly settled with where I was. Some of the lads had decided they wanted to leave and let their contracts run down, I had no issue with the boys wanting to go. Quite a few of the lads, Prince, Morgaro, Conway, Garry Kenneth, Paul Dixon… I’m not sure how many others but I’m pretty sure that all them boys left on a free when their contacts ran out, and of course there were some lads who moved on for money, but there was never anything concrete for me as far as I’m aware of. I spoke to Pat Fenlon when he got the Hibs job, obviously I’d worked with him before, had a chat with a couple of clubs but I was always under contract. You do hear certain things about clubs that might be interested, asking how you feel about a move but there was never a time when I felt I was really close to leaving.
The style of football changed once Peter Houston left and Jackie McNamara came in. Some of the football played by United between 2012-2014 was simply sublime. What was that transition like?
You looked back at some of the fellas that we’d lost over time, Barry Robson had moved on, Hunty had moved on, Goodie, Johnny Russell. Conway, Prince, Morgaro, Swannie, all moved on. So it wasn’t like we weren’t used to pushing through new players. We did have some brilliant games, some brilliant individual performances and some great team performances. I had a great time working under Jackie – a really good manager who I have a lot of time for now. A great bunch of boys. It was a younger crew and I was getting a bit older by that stage too so things were changing a bit all over, really.
That season culminated in the Scottish Cup final against St. Johnstone. What happened there?
I’m not going to say that we played really well, but if you look at the game, it comes down to fine margins. If you look at Ryan Dow’s effort, early on in the game, hits the post, goes behind the goalkeeper and out the other side. You look at their goal and it’s a poor mistake. Rado could come for that a hundred times and punch it away but it just didn’t happen that day.
What was it like leading the team out as captain at Hampden?
I’m very lucky. To do back-to-back finals as captain was obviously a massive honour. Obviously to lose both of them, it’s not fun to talk about. It was a great buzz, the whole build up, it’s a great feeling to be part of that but it’s so hard to get your head around when you don’t actually win.
You were shown a red card in the league cup final against Celtic, what are your thoughts on that decision?
I’ve got no complaints about that decision. It was a high tackle and the ball got away from me. I tried to recover it and unfortunately it didn’t work. It certainly isn’t a cup final that I look back on with fondness. You just want it to work out, you want to be one of the guys who helps bring that trophy haul from five to six. To captain the team in a cup final and walk away with nothing, that was one of the toughest things from a personal point of view. I went into that game thinking that I wanted to win, that I wanted to lift that cup as captain, so it’s a kick in the balls to not get that.
Despite Nadir Çiftçi being suspended for the final, the club still opted to sell two of their star attacking players, Stuart Armstrong and Gary Mackay-Steven. Did this anger the squad?
As far as we were concerned this had happened before at my time with the club. We’d consistently lost players and consistently brought players in. Obviously it was a big blow, but I don’t think we quite realised until afterwards how big a blow it actually was. It wasn’t ideal but I think from a fan’s viewpoint it was slightly different. Our recruitment had been good, so I expected more people to be brought in to replace the boys.
A new season brought about more poor results. How far through the season was it before you realised that this was more than just a poor year, that relegation was a very realistic possibility?
It’s hard to pinpoint the exact moment. Until relegation was confirmed I certainly thought that we were going to be alright. I genuinely felt like that; I didn’t believe for one minute that it would happen. I was convinced the whole time that we would get out of it. It was such a brutal time, even now I still don’t like chatting about it. It was tough to get my head around. That was the biggest let down, the feeling of letting down all those fans.
How hard is it to keep going? I’m sure you’re no stranger to abuse from the crowd, but it must have been even worse that season.
I understand that people get frustrated, I’ve no problem with that. It gets to a stage where you can’t do anything, you can’t do your food shopping without getting stopped. It’s not always in a nasty way; sometimes it’s just “what’s going on?”, “are we going to get out of this?”, “are we going to be alright?”. You’re trying everything you possibly can. That was without a doubt the toughest season of my career.
That season was epitomised by Gavin Gunning’s walk off against Inverness. What happened there?
I actually got on really well with Gav. The thing is, you don’t see what he does during the week. He’ll be remembered for walking off the pitch, he won’t be remembered for having excellent performances at the back. I really enjoyed playing centre back with him. The bottom line about that day was that he was struggling with injury, severely struggling. He’d been taking injections and was just having a really tough time. I think he thought that nobody was listening to him and he just had enough. He picked up the ball and he was off. He didn’t think he was actually going to be taken off and he didn’t feel like he could continue on.
In your final year with the club you were rewarded with a testimonial. Coming off a really tough year, how nice was it to have a game like this, to get the old gang back together?
Obviously that final year was not at all how I’d have liked to have finished up with the club, but the actual event that was put on, the people that put it on, it was incredible and I’ll be forever grateful to everyone in the testimonial committee that were involved in it. To see so many of the boys make it back for the game, that was one of the best things about it. Having the gaffer – the gaffers – back too. It was brilliant, the whole thing was just class.
After moving between teams a fair amount in your youth, you’d spent a decade with one club. How weird was it starting over at Montrose?
There were a few different things I had in my head with regards to moving on to a different club, in the end we decided that I could stay here, still live at home and could start thinking about what I want to do next, after football. The manager and his staff at Montrose were unbelievably good, everybody at the club was just amazing, they couldn’t do enough for us, they made it so easy. I just need to make sure that I’m doing what is best for my body so that I can keep playing for as long as I possibly can.
Once you do retire as a player, what are your next steps? Do you see yourself moving into a coaching or managerial role?
I’m coaching up at Soccerworld with an academy called Skilz, it’s a charity, I really enjoy what I do there. I’m part of the staff at Montrose as well, so I’m learning a lot more there about how things work at the club. It’s hard to tell what’s going to happen and how it’s going to work out but I’m enjoying what I’m doing at the moment and I hope to be working in the game for a long, long time.
Thanks so much for taking the time to speak with me today, Sean, I really appreciate it.
My pleasure. Take it easy pal.
Heart of Football 
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