Hydroxyl-terminated telechelic oligomeric poly (L-lactic acid), namely t-OPLLA-(OH)(n) (n = 2, 3, 4), and carboxyl-terminated telechelic oligomeric poly(L-lactic acid), namely t-OPLLA-(COOH)(2), were respectively synthesized by the copolymerization of L-lacti acid with comonomers 1,4-butanediol, glycerol, pentaerythritol, and succinic acid, while the normal oligomeric(L-lactic acid), namely OPLLA, was obtained through the self-polymerization. The effects of the type and amount of comonomer as well as the molecular weight of starting oligomer on both the generation of L-lactide and the molecular weight of residual oligomer were examined. It was found that the selectivity to L-lactide for the degradation of t-OPLLA-(OH)(n), (91.7-93.56%) was slightly larger and that for the t-OPLLA-(COOH)(2) was almost unchanged, relative to that for the degradation of OPLLA (90.3%). Both the yield of crude lactide and reaction rate for the degradation of t-OPLLA-(OH)(n) were higher, and those for t-OPLLA-(COOH)(2) were lower than for the OPLLA. An as high as 92.7 wt % crude lactide yield had been achieved for the degradation of t-OPLLA-(OH)(4), being the maximum level ever reported in the literature. With increasing the reaction time, the molecular weight of residual oligomer increased throughout for the degradation of OPLIA, and it first increased and then decreased for the degradations of telechelic OPLLA. The increase in the molecular weight of starting oligomer was unfavorable to the generation of L-lactide and also increased the molecular weight of residual oligomer. The above results indicated that the efficiency for the generation of L-lactide from t-OPLLA-(OH)(n) was obviously higher, which increased with increasing the amount of terminal hydroxyl group, and that from t-OPLLA-(COOH)(2) was lower than that from OPLLA. Possible reaction networks for the degradations of OPLLA and telechelic OPLLA were proposed.