Implementations of the present invention include drilling tools having axially-tapered waterways that can increase flushing and bit life, while also decreasing clogging. According to some implementations of the present invention, the waterways can be radially tapered in addition to being axially tapered. The axially-tapered waterways can include notches extending into the cutting face of the drilling tools and/or slots enclosed within the crown of the drilling tools. Implementations of the present invention also include drilling systems including drilling tools having axially-tapered waterways, and methods of forming drilling tools having axially-tapered waterways.