Pollen-mediated gene flow among crop cultivars and from crops to sexually compatible wild relatives is an important issue for crops with regulated markets and with traits that may impact non-target organisms. We conducted a study to evaluate landscape-level crop-to-crop and crop-to-weed gene flow in wheat. Gene flow was estimated using pollen drift from ‘Above,' a non-transgenic, imazamox-resistant winter wheat cultivar, to imazamox-susceptible wheat and jointed goatgrass (Aegilops cylindrica). Wheat and jointed goatgrass samples were collected in eastern Colorado in 2003 and 2004. Additionally, a Nelder wheel plot was sampled in 2004 to estimate gene flow to two wheat varieties and jointed goatgrass. Wheat sub samples from commercial fields were screened for resistance by treating with 44 g/ha imazamox in field plots. Jointed goatgrass and Nelder wheel samples were screened in the greenhouse. In both the field and greenhouse, hybrids were identified by an injured (stunted, tillering) phenotype and were confirmed with a PCR-based marker. In 2003 and 2004, two wheat varieties (Jagger and Prairie Red) were found to have among the highest cross-pollination rates (range 0.21 to 2.7%) out of 13 varieties sampled at distances less than 5 m from Above. Cross-pollination in wheat declined rapidly with increasing distance from the pollen source in both years. At the farthest sample distance of 37 m in 2003, average cross-pollination was 0.11% with a range of 0.0 to 0.5%. Out of 26 samples taken in 2004 from 37 to 61 m, average cross-pollination was 0.02% with a range of 0.0 to 0.12%. Negligible cross-pollination to wheat was observed at the Nelder wheel location due to asynchronous anthesis. The average cross-pollination rate for jointed goatgrass collected within the Above plot at the Nelder wheel was 0.18%. Observed hybridization rates between wheat and jointed goatgrass samples collected in or near commercial fields were low.