How will the Ultra ChillTec Silver CPU Cooler - LGA 775/1366, AM2/AM2+/AM3 compare to the CORSAIR Cooling Hydro Series CWCH50-1 120mm High Performance CPU Cooler? I will be going with the AMD Phenom II 1055T Six Core Processor and be overclocking.
For the best cooling performance, you should be looking at coolers such as the Megahalems, Venomous X, Noctua NH-D14, or Cogage Arrow. The H50 might not perform as well as the above 4 coolers (on par with the Mega though), it is more compact, and allows for better case airflow.
It's a trade-off, but for absolute performance, the 4 air coolers I listed should do the job the best.