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(1) Background: The effect of <i>Dendrobium nobile</i> Lindl. (<i>D. nobile</i>) on hyperglycemic syndrome has only been recently known for several years. Materials of <i>D. nobile</i> were always collected from the plants cultivated in various growth ages. However, regarding the efficacy of <i>D. nobile</i> on hyperglycemic syndrome, it was still unknown as to which cultivation age would be selected. On the other hand, with the lack of quality markers, it is difficult to control the quality of <i>D. nobile</i> to treat hyperglycemic syndrome. (2) Methods: The effects of <i>D. nobile</i> cultivated at year 1 and year 3 were checked on alloxan-induced diabetic mice while their body weight, diet, water intake, and urinary output were monitored. Moreover, levels of glycosylated serum protein and insulin were measured using Elisa kits. The constituents of <i>D. nobile</i> were identified and analyzed by using UPLC-Q/trap. Quality markers were screened out by integrating the data from UPLC-Q/trap into a network pharmacology model. (3) Results: The <i>D. nobile</i> cultivated at both year 1 and year 3 showed a significant effect on hyperglycemic syndrome at the high dosage level; however, regarding the significant level, <i>D. nobile</i> from year 1 showed the better effect. In <i>D. nobile</i>, most of the metabolites were identified as alkaloids and sesquiterpene glycosides. Alkaloids, represented by dendrobine, were enriched in <i>D. nobile</i> from year 1, while sesquiterpene glycosides were enriched in <i>D. nobile</i> from year 3. Twenty one metabolites were differentially expressed between <i>D. nobile</i> from year 1 and year 3. The aforementioned 21 metabolites were enriched to 34 therapeutic targets directly related to diabetes. (4) Conclusions: Regarding the therapy for hyperglycemic syndrome, <i>D. nobile</i> cultivated at year 1 was more recommended than that at year 3. Alkaloids were recommended to be used as markers to control the quality of <i>D. nobile</i> for hyperglycemic syndrome treatment.