Stiff neck,
No, not always, but for a given cartridge/rifle/load combination, yes. Some combinations of components can easily produce higher pressure, but less velocity, than another combination, in the same cartridge/rifle(for that unique individual weapon). However as a general rule when talking about a specific caliber/rifle/components combination, higher pressure means higher velocity.
This is why the different max powder charges in the book for a certain cartridge, with the same bullet, case and primer, may have very different published velocities--the pressures spike out at different levels due to many factors, not just powder and charge weight.
Just for one, two rifles made in the same factory on the same day can be very different. How? Well, for one thing, chambering reamesr do not last forever, and they ain't cheap, so they are made to tolerances, + or - so many thou. or 1/10 thou. A brand new reamer cuts the biggest (max tolerance) chamber; every time it is sharpened, it cuts a smaller chamber, until it reaches the end of it's useful life, wherein it will be cutting a minimum SAAMI spec. chamber. Two consecutive serial numbeber barrels may be cut with two different reamers, one max and one min. spec., which will result in two chambers that will perform differently with the exact same load.