The aeroelastic flutter of thin flexible webs severely limits their transport speeds and consequently the machine throughputs in a variety of paper, plastics, textiles, and sheet metal industries. The aeroelastic stability of such high-speed webs is investigated using an assumed mode discretization of an axially moving, uniaxially tensioned Kirchhoff plate coupled with cross and machine direction flows of a surrounding incompressible fluid. The corresponding aerodynamic potentials are computed using finite element solutions of certain mixed boundary value problems that arise in the fluid domain. In the absence of air coupling, the cross-span mode frequencies tightly cluster together, and the web flutters via mode coalescence at supercritical transport speed. Web coupling to an initially quiescent incompressible potential flow significantly reduces the web frequencies, substantially modifies the mode shapes, and separates the frequency clusters, while only marginally affecting the flutter speed and frequency. The inclusion of machine direction base flows significantly modifies the web stability and mode shapes. Cross machine direction flows lead to the flutter with vanishing frequency of very high cross-span nodal number modes, and the unstable vibration naturally localizes at the leading free edge. These results corroborate several previous experimental results in literature and are expected to guide ongoing experiments and the design of reduced flutter web handling systems.