Medication-overuse headache (MOH) is a challenging neurological disease, which brings frustration for sufferers and treating physicians. The patient’s lack of adherence and limited treatment evidence are frequent. The aim of this study was to compare the outcome and treatment strategies between consecutive MOH patients with daily and near-daily headache from a tertiary center. Methods: Every consecutive patient seen between January and December 2014 with the diagnosis of MOH was included. Psychiatric comorbidities, inability to inform baseline headache frequency, current or previous two-month use of preventive medications, and refusal to sign informed consent were exclusion criteria. The patients were evaluated in thorough initial consultations and divided in two groups based on their baseline headache frequency. The diagnosis and treatment strategies were clearly explained. The filling out of a detailed headache diary was requested from all patients. Endpoints compared headache frequency and adherence after two, four, and eight months between the two study groups. Results: One-hundred sixty-eight patients (31 male, 137 female) met the inclusion criteria. Nineteen patients (11.3%) were excluded. All patients had migraine or chronic migraine as primary headaches. Eighty had daily (DH), and 69 near-daily headache (NDH), at baseline consultation. Mean baseline frequency was 24.8 headache days/month (18.9 days/month for the near-daily group), average headache history was 20.6 years and mean time with >15 headache days/month was 4.8 years. Outpatient withdrawal, starting prevention, and enforcing the correct use of rescue therapy was carried out with all patients. After two months, 88% of the DH and 71% of the NDH groups adhered to treatment (p
= 0.0002). The HF decreased to 12 and 9 headache days/month, respectively in DH and NDH groups (p
> 0.05, non-significant) (Intention-to-treat (ITT) 14 DH; 12 NDH; p
> 0.05). After four and eight months, 86.3% and 83.7% of the DH patients, and 59.4% and 55% of the NDH patients were still under treatment (p
= 0.0003 and p
= 0.0001). The HF decreased, respectively, to nine and nine headache days/month in the DH patients compared to 6 and 7 headache days/month in the NDH group (p
> 0.05) (ITT, 12; 12; DH; 10; 11; NDH; p
> 0.05). Conclusions: Although open studies provide limited conclusions, withdrawing overused medications and starting prevention may have helped the favorable outcomes. However, daily headache patients had a significantly higher adherence and lower relapse rates than near-daily headache patients, despite a considerable reduced headache frequency in both groups. Additionally, real-world patient studies are scarce and the comparison between these two subsets of patients may be useful to guide clinicians in approaching their patients. Controlled studies are necessary to confirm these observations.