Python vs Groovy vs Ruby? (based on criteria listed in question)
Python has all nine criteria.  It scores a 56.
I'm sure Ruby has everything Python has.  It seems to have fewer libraries.  So it scores a 51.
I don't know if Groovy has every feature.
Since Python is 56 and Ruby is a 51, Python just barely edges out Ruby.
However, I think this kind of decision can still boil down to some subjective issues outside these nine criteria.
Considering the criteria listed below, which of Python, Groovy or Ruby would you use?

Criteria (Importance out of 10, 10 being most important)
Richness of API/libraries available (eg. maths, plotting, networking) (9)
Ability to embed in desktop (java/c++) applications (8)
Ease of deployment (8)
Ability to interface with DLLs/Shared Libraries (7)
Ability to generate GUIs (7)
Community/User support (6)
Portability (6)
Database manipulation (3)
Language/Semantics (2)