Fast forward four months and the youngster was taking his place on the bench for a crunch Europa League qualifier.
Bailey, a left-back from Telford signed a one-year contract with The New Saints in the summer, and has set his sights on the dream of every academy player – a pro career.
The full-back is one of the latest TNS youth players to make their bow for the first team, after a promising two years with the age-group sides, including twice reaching the FAW Youth Cup Final – once losing to Swansea and then this year suffering the frustration of seeing the game cancelled due to the pandemic.
His first start for the club came last season at 17 in a 6-2 win at Carmarthen, and the 18-year-old said he remembered the nerves at being called up to train with the first team.
“I remember getting the message the night before,” he said. “It just said ‘you’re with the first team tomorrow at 9am’. I was so nervous. It was such a good feeling but such a nervous one too.
“You see them winning the league all the time, you see how good they are then you have to get ready to be playing with them, it’s a great feeling.”
The call-up to the first-team was great news, but there was another call-up that Bailey had no choice but to turn down – one to play for Wales.
Despite being asked to join one of the Welsh youth squads, he has no Welsh blood in his family.
He said: “I wanted to go, I was gutted. My mum was ringing up everyone in the family asking if we had any Welsh blood but I had to turn it down.”
Having been picked by manager Scott Ruscoe to start TNS’s first game of the season, Bailey was then selected on the bench for the side’s disappointing Europa League exit to B36 Torshavn in the Faroe Islands
The experience saw him travel with the squad to the Faroe Islands, and included the classic football club ritual of performing his initiation song in front of the squad – the left-back chose Nelly’s ‘Dilemma’ for his effort.
As the squad enjoyed a meal in a restaurant, former Wales international, TNS legend and current assistant manager Steve Evans told the youngster he was up.
Bailey said: “I was thinking I don’t want to do this and then they came in so I thought let’s have it and proper went for it. I said ‘I am Josh Bailey and I am from a beautiful place called Telford’ and went for it. It was great, everyone was singing along.”
The actual game proved a crushing disappointment with the Saints losing out on penalties, and although he remained on the bench Bailey said the experience has made him more hungry to succeed.
He said: “I was desperate to get on, just even for a couple of minutes but even being on the bench, knowing the manager had the trust in me if he needed me to come on was amazing.”
Bailey said the focus is now on getting as many minutes of men’s football as possible, and improving.
He said: “I have been at youth level and never really played men’s football. I just want to get the experience, get used to the physicality, the speed and the strength, and develop as a player.”
He added: “When I was with the youth it is easy to keep hold of the ball, now you have to pop it off quickly because you know someone will be coming through the back of you.
“I feel that I have improved so much as a player just from playing with the first team, my whole physicality has changed. I just want to work hard and make the most of my chances and earn myself that next contract.”