This paper focuses on the small-signal stability analysis of systems modelled as differential-algebraic equations and with inclusions of delays in both differential equations and algebraic constraints. The paper considers the general case for which the characteristic equation of the system is a series of infinite terms corresponding to an infinite number of delays. The expression of such a series and the conditions for its convergence are first derived analytically. Then, the effect on small-signal stability analysis is evaluated numerically through a Chebyshev discretization of the characteristic equations. Numerical appraisals focus on hybrid control systems recast into delay algebraic-differential equations as well as a benchmark dynamic power system model with inclusion of long transmission lines.