Urban drainage infrastructures’ life-cycle management and associated complex decision makingrnprocesses require exploitations of the benefits of advanced digital-technologies and/or spatialrndecision support systems. But, actually how this hypothetical concept can be materialized in linernwith varying ground contexts and other related factors do require investigation and scientificrnreasoning. And thus, the purpose of this study is to model an urban storm water drainagerninfrastructure maintenance management scheme through a Web GIS-Based Decision SupportrnSystem (WGBDSS) taking the case of Nifas Silk Lafto sub-city of Addis Ababa. In this theme, thernstudy explores the synergy between WGBDSS and drainage infrastructure maintenancernmanagement core issues through integration of drainage infrastructures’ physical conditionrnassessment, current drainage management practice of study area, hydrologic analysis, webrntechnology, Multi-Criteria Decision Aids (MCDA) and Analytic Hierarchy Process (AHP) methodrnfor analysing and organizing complex decisions based on objective standards of judgment. WebrnGIS-based decision support tools that exploit multi-criteria matrices for optimization algorithms ofrnstructured query language (SQL) were also utilized. In addition, starting from data collection tornfinal output production of the overall study, freely available softwares and open source resourcesrnhave been exploited. Besides, ArcGIS, PostgreSQL, PostGIS, Survey Master and Kobo toolboxrnmobile applications, Global mapper, and surveying equipment like Differential Global PositioningrnSystem (DGPS-RTK; for drainage routes’ locational information collection) were utilized in datarnprocessing, analysing, and presentation. On top of this ApacheTomcat, Open layer, GeoServer, maprnstore were also used to publish the geospatial database and related outputs on developed portal ofrnthe Web GIS platform. Moreover, slope analysis, the runoff flow direction, flow accumulation,rnwatershed delineation and flood vulnerable area identification, and the like hydrologic analysisrnwere thoroughly performed and respective maps were also produced using desktop ArcMaprnapplication. The findings of basic and advanced physical condition assessment of drainagernnetworks of the study area revealed that 80% of urban drainage routes out of the total networksrndemand repair type of intervention, 8% of drainage structures call for upgrading type ofrnintervention, another 8% require for replacement and the rest 4% demand for planned type ofrnmaintenance. Eventually, the final result of this study implies that decision making through rankingrncompeting and complex problematic drainage networks for maintenance prioritization purpose needrna paradigm shift from the conventional drainage infrastructure life-cycle management approach (i.e.rnmore of “fix when failedâ€) to WGBDSS.