A series of new 1,4-dihydroindeno[1,2-]pyrazole tethered carbohydrazide hybrids () were designed, synthesized and evaluated for their antimicrobial activity. Compounds , , , and demonstrated significant activity against the entire panel of test pathogens. Further, compounds and exhibited significant anti- activity. These potential hybrids ( and ) also exhibited promising ergosterol biosynthesis inhibition against , which was further validated through molecular docking studies. Furthermore, compounds and caused intracellular ROS accumulation in MTCC 3017 and were non-toxic to normal human lung cell line MRC5. studies revealed that they demonstrated drug likeness and an appreciable pharmacokinetic profile. Overall, the findings demonstrate that and may be considered as promising leads for further development of new antifungal drugs.