We use a Generalized Additive Model (GAM) to provide the first winter sea ice concentration record from two cores located within the southwest Pacific sector of the Southern Ocean. To compliment the application of GAM, a time series analysis on satellite records of sea ice concentration data was used to extend the standard 13.25 year time series used for paleoceanography. After comparing GAM sea ice estimates with previously published paleo sea ice data we then focus on a new paleo winter sea ice record for marine sediment core E27-23 (59-37.1'S, 155-14.3'E), allowing us to provide a more comprehensive view of winter sea ice dynamics for the southwest Pacific Ocean. The paleo winter sea ice concentration estimates provide the first suggestion that winter sea ice within the southwestern Pacific might have expanded during the Antarctic Cold Reversal. Throughout the Holocene, core E27-23 documents millennial scale variability in paleo winter sea ice coverage within the southwest Pacific. Holocene winter sea ice expansion may have resulted from the Laurentide Ice Sheet deglaciation, increased intensity of the westerly winds, as well as a northern migration of the Subtropical and/or Sub-Antarctic Fronts. Brief consideration is given to the development of a paleo summer sea ice proxy. We conclude that there is no evidence that summer sea ice ever existed at core sites SO136-111 and E27-23 over the last 220 and 52,000 years, respectively.