Carbon-14 in tree rings have suggested that there had been multiple extreme solar proton events (SPEs) in the past. While the largest events such as in 774–775 CE can be significantly detected by the typical precision of accelerator mass spectrometry, smaller but possibly more frequent events have been difficult to be detected. Thus, the frequency or any characteristics of such relatively smaller events are still largely unknown. In this paper, we report that multiple large SPEs had occurred before the onset of the Wolf grand solar minimum based on high-precision carbon-14 analyses. It is suggested that they had occurred at the maximum and the declining phase of solar cycles, and that they had occurred during the transition time of solar activity into a deep minimum. We propose that this episode may provide a unique opportunity to elucidate a potential interaction between the solar dynamo and extreme solar flares.