The effect of two superplasticizers (SPs) with various equivalent (eq.) alkali contents (i.e., with 0.00009% and 4.1% of Na2Oeq, respectively) on the development of an alkali-silica reaction (ASR) was investigated through the use of multilevel assessment. This testing protocol showed promising results for evaluating concrete damage due to ASRs based on mechanical and microscopical testing protocols, specifically the stiffness damage test (SDT) and the damage rating index (DRI). Concrete specimens that incorporated the aforementioned SPs and distinct reactive aggregates (coarse and fine) were manufactured and then stored in conditions that enabled ASR development and were monitored over time. Upon reaching the desired expansion levels of this study, the concrete specimens were prepared for the multilevel assessment. The results show that the SP-incorporated concrete specimens with lower and higher alkali content yielded lower and higher deterioration results, respectively. This clearly confirms that while SP-incorporated concrete that contains SPs with a higher alkali content could increase the risk of ASR deterioration, those SPs with a very low amount of alkali content could act as a mitigation strategy against ASRs. Finally, an investigation into the influence of distinct SPs on the chemical composition of an ASR gel was conducted, which confirmed that the SP with a higher alkali content had the highest potential for further deterioration.