Background: Kickboxing is a combat sport that encompasses various forms of competition. K1 kickboxing is conducted without any restrictions on the force of strikes, and the bout can end prematurely through a knockout. Headgear has been introduced in amateur kickboxing to safeguard the head. However, scientific studies have shown that despite their use, serious head injuries can still occur. The aim of this study was to evaluate the temporal structure of the bout by calculating the number of head strikes in K1 kickboxing bouts with and without headgear. Methods: Thirty K1 kickboxing bouts were analyzed, with 30 participants included in the study. The fights were conducted according to the World Association Kickboxing Organization (WAKO) rules. The bouts consisted of three rounds of 2 min each, with a 1 min break between rounds. Sparring pairs were arranged according to weight categories. The first bouts were conducted without headgear, and two weeks later, the fights were repeated with WAKO-approved headgear. The number of head strikes was assessed retrospectively by analyzing video recordings of the bouts, categorizing strikes as hand or foot strikes, and differentiating between strikes that hit the head directly or indirectly. Results: The results showed statistically significant differences between bouts with and without headgear in terms of the number of strikes to the head (p = 0.002), strikes directly to the head (p < 0.001), all hand strikes to the head (p = 0.001), hand strikes directly to the head (p = 0.003), and foot strikes directly to the head (p = 0.03). Higher values were observed in bouts with headgear. Conclusions: Headgear increases the probability of direct strikes to the head. Therefore, it is important to familiarize kickboxers with the use of headgear in their sport to minimize head injuries.