Prestressed segmentally constructed balanced cantilever bridges are often subjected to larger deflections than those predicted by calculations, especially for long-term effects. In this paper, the case of modular balanced cantilever bridges, which are prestressed segmental bridges obtained through a repetition of the same double cantilever, is investigated. The considered bridges are two typical cases of modular balanced cantilever both subjected to large deformations during their lifetime. In this case, due to the unusual employed static scheme, creep deflections indefinitely evolve over time particularly at the end of the cantilevers and in correspondence with the central joint. These remarkable deflections cause discomfort for vehicular traffic and in certain cases can lead to the bridge collapse. Important extraordinary maintenance interventions were necessary to restore the viability of the bridges and to replace the viaduct design configuration. To this aim, the static schemes of the structures were varied, introducing new constraints, new tendons, and carbon fiber reinforcements. In the present work, time analysis was performed to compare the time-dependent behavior of the bridge according to two different creep models, the CEB-FIP Model Code 2010 and the RILEM Model B3, with the real-time-dependent behavior of the bridge observed during its lifetime. The two different employed models exhibit different behaviors in terms of displacements and bending moments acting on the bridge. Interesting considerations are made on their reliability in simulating the long-term creep effects that evolve indefinitely over time. Moreover, retrofitting techniques have been proposed and modeled to predict their effectiveness in reducing time-dependent deflections.