Winter conditions can lead to rapid dehydration and cracking of teat tissue, thus increasing mastitis risks. The objectives of these three winter trials were to compare application of a new novel commercial winter teat dip (1% iodine, 50% glycerine) to three existing commercially available winter teat dips and best management winter milking practices. Overall results for the 3 trials showed similar teat skin and end conditions (except teat skin in trial 5) for the 1% iodine, 50% glycerine dip as compared to 3 commercial winter teat dips. There were significant improvements in teat skin and end conditions over time for all dips, primarily related to weather and increasing temperatures. There were also significant differences in teat skin and end across days within barn with the same dip. Although dips can affect teat health, these figures substantiate that animal stage of lactation, barn or facilities, and environmental exposure (temperature / time exposure) have tremendous bearing on dip effects. None of the treatments were effective in completely alleviating teat end changes due to weather.