I've never tried to over-clock one of my Mac by myself, but about 8 months ago, I bought a used 2009 8 core Pro from OWC that had been overclocked from 2.66 to 3.32. I have no idea how it was done, but it has been running stable all that time with no issues of incorrect time display etc. I haven't done any formal benchmarking, but there's no question this rig is quite a bit zippier than any other Mac Pro tower I've run.
At first, there were two situations that would cause total an overtemp freeze/system crash: 1) Attempts at long rips in Handbrake (which I've confirmed as a known issue in some video forums) and 2) certain heavily loaded scenarios in Flight sim X running under boot camp.
After reading up on a wild liquid cooling solution, I tried the simple approach first: I downloaded one of the free fan-control utilities ( I use "Macs Fan Control" which is also available in a Windows version specifically for boot camp and has a read-out on all the measured temps in the Mac.) I now manually turn up the main input and exhaust fans and the A and B core booster fans to near their max for either of the above situations. The fan noise is certainly very un-Mac-like, but the CPU cores stay down below 70c and I can run either of the above apps all day with no issues.