Vapor–liquid–solid processing of boron nanowires (BNWs) can be carried out either using a bottom-up or top-down growth mode, which results in different contact modes between the nanowire and the substrate. The contact mode may strongly affect the electrical transport and field-emission performance of the individual boron nanowires grown on a Si substrate. The electrical transport and field-emission characteristics of individual boron nanowires of different contact modes are investigated in situ using a scanning electron microscope. The contact barriers are very distinct for the different contact modes. Moreover, the transition from a “contact-limited” to a “bulk-limited” field-emission (FE) process is demonstrated in nanoemitters for the first time, and the proposed improved metal–insulator–vacuum (MIV) model may better illustrate the nonlinear behavior of the Fowler-Nordheim (FN) plots in these nanoscale systems. Individual BNWs with different contact modes have a discrepancy in their emission stability and vacuum breakdown characteristics though they have similar aspect ratios, which suggests that their electrical transport and field-emission performance are closely related to their contact mode. Boron nanowires grown in the base-up mode have better field-emission performances and are more beneficial than those grown in the top-down mode for various device applications.