The answer is always yes but highly unlikely.
In order for there to be Static Shock release you have to have an object that has a lower or higher reference voltage than your body has. Lets say the object is your motherboard. If it is sitting at lets say +3v to earth ground and your body is at +10000v you will have a static discharge into the motherboard and can cause damage depending on where you touched the board. The reason for such high voltage is that the current of these discharges is so low that the voltages have to overcome your bodies resistance which is different from person to person. This is why a static charge does not kill you and it has to be over your hart and so on. That said the components in your system are much more sensitive and can be damaged from a shock like that.
Ok that being said, if you set your bodies voltage equal to the that of the item you are working on then there will me no difference in potential and thus not static release. You do this by either keeping one hand on your system at all time to ensure you potential does not change or you use a static strip which will keep you always connected to the object you are working on. If you touch ground or a grounded object before working on it this will bring your bodies voltage close to 0v in reference to the object then connect a static strip from you to the object you are working on then you should be safe.
Ok, now that that is out of the way, a lot of techs don't even bother with a grounding wire because if you are careful not to build up static while working (walking across carpet or plastic) and once you have discharged your body once, then you should be relatively safe. This is why all techs say, "touch the case before you start working on your computer" to get that initial discharge, equalizing you with the case which the motherboard is grounded to through the brass standoffs.
Hope that helps. You will get a lot of opinions on this subject though.