Background/Objectives: The double-kissing (DK) culotte technique is a modification of the culotte technique that employs initial kissing balloon inflation after first stent implantation. The DK culotte technique may improve strut apposition and procedural outcomes; however, data on its efficacy and safety remain limited. This study aimed to investigate the short-term outcomes of bifurcation percutaneous coronary intervention (PCI) using the DK culotte technique compared with those of the culotte technique in patients with acute coronary syndrome (ACS). Methods: This two-center, observational, retrospective study included patients with ACS. Out of 12,132 screened patients, 117 and 122 underwent DK culotte and culotte PCIs, respectively, with 117 and 57 patients remaining after propensity score matching. The primary endpoint was 1-year target lesion failure (TLF), which included cardiovascular death, target vessel myocardial infarction or clinically indicated target lesion revascularization (TLR). Secondary endpoints included major adverse cardiac events (MACEs) comprising myocardial infarction, cardiac death, and TLR; contrast medium amount (mL); and cumulative radiation dose (mGy). Results: At 1 year, TLF occurred in 7% and 12% of the DK culotte and culotte groups, respectively (p = 0.17). No significant differences were observed in MACEs between the groups (13% DK culotte vs. 19% culotte; p = 0.12). Additionally, the DK culotte technique did not cause higher contrast medium usage or cumulative radiation dosage. Conclusions: No statistically significant differences were found in TLF and MACE reduction between ACS patients treated with the DK culotte technique and the culotte technique. The observed trend favoring the DK culotte needs further validation in prospective studies.