Bareroot and containerized loblolly pine (Pinus taeda L.) were planted in December 2016 and February 2017 to compare performance across four sites in South Carolina and Georgia. Main treatments analyzed for growth differences were stocktype, genetics, and planting date. Analysis of variance results showed significant growth differences after two growing seasons for containerized over bareroot seedlings, for control-pollinated seedlings over open-pollinated and varietal seedlings, and for December-planted seedlings over February-planted seedlings. Control–pollinated seedlings demonstrated the most incremental growth between ages one and two. Site conditions dictated seedling survival to a certain degree, and bareroot seedling growth was slightly better than containerized on the least stressful site. Results uncover important trends for main effects of stocktype, genetics, and planting date, but also underscore the importance for land managers to avoid blanket reforestation prescriptions, with more emphasis placed on site-specific conditions.