Purpose: The aim of this study was to evaluate the effects of active preconditioning techniques using blood flow restriction or/and systemic hypoxic exposure on repeated sprint cycling performance and oxygenation responses. Methods: Participants were 17 men; 8 were cycle trained (T: 21 ± 6 h/week) and 9 were untrained but physically active (UT). Each participant completed 4 cycles of 5 min stages of cycling at 1.5 W⋅kg–1 in four conditions [Control; IPC (ischemic preconditioning) with partial blood flow restriction (60% of relative total occlusion pressure); HPC (hypoxic preconditioning) in normobaric systemic hypoxia (FIO2 13.6%); and HIPC (hypoxic and ischemic preconditioning combined)]. Following a 40 min rest period, a repeated sprint exercise (RSE: 8 × 10 s sprints; 20 s of recovery) was performed. Near-infrared spectroscopy parameters [for each sprint, change in deoxyhemoglobin (Δ[HHb]), total hemoglobin (Δ[tHb]), and tissue saturation index (ΔTSI%)] were measured. Results: Trained participants achieved higher power outputs (+10–16%) than UT in all conditions, yet RSE performance did not differ between active preconditioning techniques in the two groups. All conditions induced similar sprint decrement scores during RSE in both T and UT (16 ± 2 vs. 23 ± 9% in CON; 17 ± 3 vs. 19 ± 6% in IPC; 18 ± 5 vs. 20 ± 10% in HPC; and 17 ± 3 vs. 21 ± 5% in HIPC, for T and UT, respectively). During the sprints, Δ[HHb] was larger after IPC than both HPC and CON in T (p < 0.001). The Δ[tHb] was greater after HPC than all other conditions in T, whereas IPC, HPC, and HIPC induced higher Δ[tHb] than CON in UT. Conclusion: None of the active preconditioning methods had an ergogenic effect on repeated sprint cycling performance, despite some specific hemodynamic responses (e.g., greater oxygen extraction and changes in blood volume), which were emphasized in the trained cyclists.