The fungus Clonostachys rosea is widely distributed all over the world. The destructive force of this fungus, as a biological control agent, is very strong to lots of plant pathogenic fungi. As part of the ongoing search for antibiotics from fungi obtained from soil samples, the secondary metabolites of C. rosea YRS-06 were investigated. Through efficient bioassay-guided isolation, three new bisorbicillinoids possessing open-ended cage structures, tetrahydrotrichodimer ether (1) and dihydrotrichodimer ether A and B (2 and 3), and 12 known compounds were obtained. Their structures were determined via extensive NMR, HR-ESI-MS, and CD spectroscopic analyses and X-ray diffraction data. Compounds 1–3 are rare bisorbicillinoids with a γ-pyrone moiety. The biological properties of 1–15 were evaluated against six different Gram-positive and Gram-negative bacteria. Bisorbicillinoids, 2–5, and TMC-151 C and E, 14 and 15, showed potent antibacterial activity.