Once again, this evening a frustrated Ashley Cole will be forced to watch on from the sidelines as he continues his recovery from injury, but League Cup fixtures are always sure to evoke many memories for the left-back.
It was in this competition that he made his Gunners first team debut, as an 18 year-old, in the Fourth Round of the old Worthington Cup against Middlesbrough - six years ago tomorrow.
The following season he played in the Third Round match against Ipswich, the day after his former youth coach, and popular Gunners legend, George Armstrong died from a brain haemorrhage on the training pitches.
So tonight's occasion is sure to have Ashley reminiscing, especially as Reading's James Harper was in the same year as him in the Arsenal Academy, and the Royals' Steven Sidwell and Graham Stack also played in the same youth and Reserve teams as Ashley during their Arsenal days.
What are your memories of your first team debut in 1999?
Well I came on as a substitute for Ray Parlour and played the whole of extra-time. There were a lot of youngsters involved that day, but also a lot of first teamers too. There were a few big names in the team, for example Thierry played in that game. For me just to be there with them was a great achievement, I didn't think I was going to get on. But I came on at left-back and it was a fantastic experience, and great to have my debut in front of a big crowd. It was just a shame we got knocked out on penalties. It was a really proud moment for me. I was training with those players every day but just to get out there and finally play was magnificent and the start of a long road for me.
The following year we lost 2-1 at home to Ipswich in the Third Round, what was that occasion like?
Obviously that was the day after George Armstrong died, and a lot of the players who played that day came through under him. So that was very hard to take, it was a very sad moment. I was getting ready at home when I got a call from Paolo [Vernazza] saying that Geordie had died. It was hard to focus on the game and we all wanted to win it for him, so we were upset to lose. But I think he would have been proud of the way we played that day, and you have to give him a lot of credit because there were eight or nine youngsters in the Arsenal team that day and we are all playing at a good level now.
It's good to see so many of Arsenal's academy products from the last four or five years make successful careers for themselves isn't it?
Yes, definitely. To make it here is very hard, and you need a little bit of luck too. There are always established players ahead of you but look at the players who have gone on to make it elsewhere. Jermaine Pennant is doing really well, Julian Gray, Tommy Black and Matty Upson to name just a few, they have done really well. I still keep in touch with a few of them, like Upson, Pennant, Paolo, David Noble, Jay Bothroyd and Julian sometimes too. Then there is Sidwell, Harper and Stacky at Reading.
I think James Harper and Siddy will come back to Highbury looking to prove a few things so it's definitely going to be a tough game. I think we can come through it and go through to the next round, but I really hope Reading do well in the league this season.
Reading are doing very well under Steve Coppell's guidance at the moment. What was he like to play for when he managed you during your loan spell at Crystal Palace?
He was amazing for me. Whenever I speak to Stacky, I always tell him to say hello to Steve Coppell for me because I really loved playing under him and I'm thankful for everything he did for me. He really helped make me what I am now. He gave me the chance to go on loan at Palace when no-one had heard of me, so I'm grateful he took that chance. And he was such a great manager, brilliant, everyone got on with him and I think I really owe him.
As one of the more experienced players at the Club now, do you ever have any words of advice for our youngsters?
I've spoken to a few of them. I just tell them to keep going, and not to be afraid when they join the first team. At the end of the day, it's your life, and if you want to make a career out of it you can't be scared to put in a tackle or anything. Don't be scared, that's the main thing. Really I don't get too involved, but if they come to me then of course I'm happy to talk to them.
What's the latest on your injury Ash, any news on when you might come back?
No, we just have to assess it every two weeks. I'm wearing the supportive boot all the time. I am working in the gym, doing weights and on the bike, but until I can take the boot off I can't jog or anything like that. I haven't had any setbacks, it's just taking time to heal.
Is it a metatarsal bone in your right foot?
Yes, in fact I played with the injury for a month and a half, because I didn't really know what it was at first. I was just putting ice on it every day because I thought it was just a knock. Then I said to Gary Lewin that it was hurting, and that night it began to ache. So I had a scan before the Ajax game, but the scan just showed it was bruised so I thought nothing of it and played against Ajax.
Then I had an X-ray on it just before I joined up with England and after that Gary said I couldn't play with the injury because it could break all the way. It's annoying. I haven't missed too many games so far but I think I will end up missing quite a few now. At the start of the season I felt really fit, and I said to the physios, which probably jinxed it, that I was hoping not to miss a game all season. Then that happened and I was gutted.
And your understudy Gael Clichy then picked up the same injury while playing for France Under-21s.
It's unbelievable, just crazy. It's the same foot as me, and the surgeon said to me when I did mine he hadn't seen anything like it in 25 years - then Gael does the same thing. It's one of those things, but I feel so sorry for him. He's just getting his chance in the team and then that happens.