He also picked up FAI Cup and League Cup medals and scored three goals in European competition for City.
But he has been restricted by a knee injury this season and if another operation – his third – is not successful then he will be forced to quit.
"If I don't get any relief from this then it looks like I could be done playing. It could be the end of my playing career," said Deery (right).
"I've been having trouble with my knee for quite some time now. My knee is constantly aching. I had a severe operation called patella stabilisation surgery last year and I don't think I set myself up mentally to prepare for that in terms of how long I was going to be out. They opened up the side of my knee about an inch or two and put a stitch in my kneecap.
"So that was very traumatic last year and I struggled to get my head around it for a couple of months. I had a clean-out of the knee at the start of February and I probably did come back a bit too quick after that.
"I know my knee is not in great shape and it has to be managed at this stage of my career. To get another steroid injection would only be a short-term solution.
"So I have been in contact with the surgeon and he's happy to do a scope and see what's causing the pain and nullify it.
"I'm coming 29 years old in December and I should be hitting my peak. I know with the operations that I've had and the luck I've had, that won't be the case.
"Hopefully I can still have a big say in the Derry City team and helping them be successful. I'm clinging on to a bit of hope that the surgeon will tell me after this operation that, if I'm managed right, there's no reason why I can't play for a year or two. At the end of the season I will re-evaluate everything and spend a bit more time with my family and think about it.
"Yes, this could be my last season with Derry but I still have a bit of hope that there could be a success story after this operation."