Amputee Football (AF) players move using lofstrand crutches (LC) and a single leg during training and matches, which may expose them to excessive loads. Due to a lack of scientific articles describing these issues, this pilot study aims to gain insight into the assessment of pain experiences, as well as external loads during training and matches in AF. An observational study design was followed. Twelve male AF players (2 goalkeepers—GK and 10 field players—FP), 29.9 ± 8.7 years, stature 178.3 ± 6.5 cm, body mass 77.2 ± 8.9 kg were involved in the study. After stature and body mass measures, participants filled out the questionnaire for pain. The players were familiarized with digital pain drawing (DPD). Afterwards, they reported pain typically felt in relation to regular AF training and playing matches—recall pain (RP). During a two-day training camp (TC) with two training sessions each day and during a two-day international tournament (IT) with two matches each day, the players were monitored using DPD, rate of perceived exertion (RPE) and overall pain level (OPL) scales. In addition, during an international tournament (IT), match players were monitored using a GNSS tracking system for external load assessment. All of the participants reported multiple locations of pain after AF training or a match. The area of recall pain (RP) was the highest: +0.5% when compared to the end of TC and +43% when compared to end of IT. The pain area registered at the end of IT was significantly lower (p = 0.028) compared to RP and lower without statistical significance when compared to the end of TC. Average RPE was 3.31 ± 1.38 and average OPL was 2.86 ± 1.81 in 0–10 scale. Typical RPE was higher than that registered at the end of IT. Also typical OPL was higher compared to that registered after the end of TC, which was higher than after the end of IT. The average distance covered by a FP during a match ranged from 2483.14 ± 583.64 m to 2911.08 ± 828.90 m. AF field players suffered pain as a consequence of training and matches. The loads coming from playing and training, combined with pain, may lead to injuries. Further research directions should include assessments of the relationship of pain characteristics, injuries and GNSS tracking parameters.