The skin plays various crucial biological functions and gradually degenerates due to the process of skin aging. Hence, the development of new ingredients for delaying or even reversing skin aging is an essential subject that needs to be addressed. Our screening effort for anti-skin aging ingredients has led to the discovery that Sideritis scardica extract (SSE) possesses collagenase inhibition, advanced glycation end product (AGE) formation inhibition, antioxidative, and antiallergic activities, as well as ultraviolet B (UVB)-induced matrix metalloproteinase-1 (MMP-1) expression inhibition activity. However, the effect of S. scardica, commonly known as a mountain herb, on skin aging is unknown and needs additional study. Further studies on SSE have led to the isolation of 3 flavonoids with an uncommon 8-hydroxyl moiety, isoscutellarein (1), 4′- O-methylhypolaetin (2), and 4′- O-methylisoscutellarein (3). Biological evaluations also revealed that 1-3 possess SSE collagenase inhibition, AGE formation inhibition, antioxidative, and antiallergic activities, while 3 was identified to possess SSE UVB-induced MMP-1 expression inhibition activity. Moreover, the AGE formation inhibition activity and antiallergic activity of 1-3 were speculated to be derived from their antioxidative activity, while direct inhibition of the collagenase enzyme led to their observed collagenase inhibition activity. Regarding the inhibition activity of 1-3 on UVB-induced MMP-1 expression, further studies are necessary to reveal their possible mechanism of action. Collectively, the biological activities of SSE and the isolated flavonoids 1-3 highlight the potential of S. scardica to be further developed as an agent to delay or reverse skin aging.