The day had started at the Riverside full of hope. The sun had not long risen and Fry and his mates were getting on a bus and were Wembley bound.
When they got back on that bus later in the day, Boro had lost to Norwich City in the play-off final and the journey home for Fry was long, painful and often silent.
Little did he know at the time that just three months later, his journey as a Boro first team player would begin. And here we are, 10 years later, sat in the Rockliffe press room reflecting on all that’s gone before and looking ahead to what he hopes comes in the future.
“That was gutting that play-off final, wasn’t it,” he says.
“I remember before the game all you could see was red and Boro fans everywhere outside Wembley. It was a long journey home.”
He has happier memories as a fan in the stands.
“The one I remember was when we beat Man City in the cup, the Lee Tomlin turn. I was there, what a day that was.”
When Fry was growing up, he’d take his autograph book to the Riverside and to Rockliffe. He still remembers the buzz when Jimmy Floyd Hasselbaink stopped his car, wound his window down and signed it.
“I remember when I had a season ticket watching Jonathan Woodgate,” he says.
“What a player. I’m not just saying this now because he’s a coach here, but how good was he?! He never used to sprint. He was always just there in the right place.
“I remember I saw him out out and about a few times in his car when I was younger and I was buzzing.
“Woody was still in the first team when I started training and he was sound with me.
“One thing I’ll always remember, the first day I trained he was talking to me all the way down as we walked to the training pitch and then when we got on the pitch he just changed.
“I was playing with him at centre-half and he was going mad with me. I remember thinking what’s going on here, you were being sound with me a minute ago. Then when we finished again, he was sound again, chatting away. I think that’s what I learned, when you step over that line, the biggest thing is winning.”
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And Fry won as a youngster. There was the European Under-17 Championships with England in 2014 and the Under-17s World Cup three years later. Then came the Toulon Tournament with England’s Under-21s the following year, when Fry was named in the Team of the Tournament.
“To be fair, a few weeks ago I actually had a look at that team and most are still playing at a decent level,” he says.
“Our squad was really good. There was Ezri Konsa, Fikayo Tomori at AC Milan. I was starting as well. It’s another thing I’m proud of.
“I look back on those memories, absolutely fantastic. When you’re there in a tournament like that you never want to leave. And I’m still in contact with some of the lads today. I’ve made friends forever.”
Some of his best mates are in the Boro dressing room.
“We do a lot as a group, the dressing room is fantastic, honestly,” he says.
“Everybody gets on with each other. If there’s a disagreement on the pitch, it’s spoken about after and forgotten about. It’s a really good group.”
The dressing room pool table is always in use after training. Dan Barlaser is rarely beaten. The darts board gets a good hammering as well.
“I’m not just saying this, but I’d say I’m the best at darts,” laughs Fry.
“I have my own darts! Out of the lads in the dressing room, I’m the best. I’m not great but I’m the best here.”
A squad coffee club is also in its infancy.
“It only just started a couple of weeks ago,” says Fry.
“The lads went for one in Yarm last week. We went for a coffee yesterday actually, over at the golf club.
“There was me, Tommy, Hayden, Aidan, George, Riley, Tom Glover. It’s only half an hour or so, bit of a chit-chat and then shoot off. I want to get home to the bairn.”
Fry’s daughter is two now.
“The best thing to ever happen to me was having my little girl,” he says.
“It just gives you that little extra boost. I look at life a lot different now.
“It motivates me, even though it is tough, especially the first year and a half. We’re lucky that we have family in the area.
“She’s two-year-old now, running about, I just absolutely love it.
“She doesn’t really have a clue what I do, but I’ve managed to make her say ‘Up The Boro!’. And when I say I’m going to work she points at the badge. She likes kicking a football about in the garden.
“As she gets older she’ll understand more.”
Fry was one of the special guests at a sold-out Lakes Social Club last week for the second of Boro’s On the Road events. On stage alongside Barlaser and boss Michael Carrick, one of the questions he was asked was whether he’d ever come close to leaving the club and his answer was an emphatic no.
The next day he discussed why.
“I just feel like I’m from Middlesbrough, all my family are from here, I love it here,” he says.
“We achieved promotion in that first year [2016] but I didn’t play too much and I was young at the time.
“I still feel like I owe a lot to the club. I want to get promotion. I feel like if I ever did leave and we hadn’t won promotion I’d really regret it.
“Me being a local lad, knowing how much it means to everyone in the area. Hopefully we can achieve that again as a team.
“I see how much of an impact it has on the fans when we’re doing well and it’s the same if we’re not doing well. I’ve had all sorts when I’ve been out and about, fans always want to talk. But I don’t mind that, I was the same when I was young.
“It is hard sometimes because I might get home and we’re going through a tough period and my missus will say we need to pop to B&M. I’ll put my cap on but I’ll still get recognised.
“But it never ever bothers me. It’s good and I’m quite open. Sometimes I probably say too much and give too much away, but I have time for anyone. If anyone ever wants to talk to me, I never mind.
“I’m from the area, I love the area, it’s part of being a local lad in the team.
“That promotion still means so much to me. My dad has my medal. He has my Euros and World Cup medals as well.
“I said when I moved house I’d get them all but I think he’s more attached than I am. I just pop him a text every now and again and make sure he’s looking after them.
“I think he’s more proud of them than I am. Hopefully I can get another one for him this year.”
