| No | Bupati (Nama lain) |
Mulai Jabatan | Akhir Jabatan | Prd. | Ket. | Wakil Bupati | ||||
| 1 | Panembahan Ronggo Sukowati | 1530 | 1616 | 1 | — | |||||
| 2 | Pangeran Purboyo & Pangeran Jimat | 1616 | 1624 | 2 | ||||||
| 3 | Pangeran Megatsari | 1624 | 3 | |||||||
| 4 | R. Kanoman R.T.A. Wirosari Ghung Seppo Sumenep |
1685 | 4 | |||||||
| 5 | R. Dhaksena R.T.A Adikoro I |
1685 | 1708 | 5 | ||||||
| 6 | R. Sasena R.T.A. Joyonegoro |
1708 | 1708 | 6 | ||||||
| 7 | R. Asral R.T.A Adikoro II |
1708 | 1737 | 7 | ||||||
| 8 | R. Sujono R.T.A Adikoro III |
1737 | 1743 | 8 | ||||||
| 9 | R. Ismail R.T.A Adikoro IV |
1743 | 1750 | 9 | ||||||
| 10 | R.T.A. Adiningrat | 1750 | 1752 | 10 | ||||||
| 11 | R. Alsari R.T.A. Cokroadiningrat I Ghung Seppo Pamekasan |
1752 | 1800 | 11 | ||||||
| 12 | R. Alsana R.T.A Cokroadiningrat II Ghung Tenga |
1800 | 1804 | 12 | ||||||
| 13 | R. Palgunadi Pangeran Mangku Adiningrat |
1804 | 1842 | |||||||
| 14 | R. Banjir Pangeran Adipati Arya Surya Kusumo Raganata |
1842 | 1854 | |||||||
| 15 | R. Ario Moh. Hasan | 1854 | 1891 | |||||||
| 16 | R. Ario Abdul Aziz Pangeran Mangunadiningrat |
1891 | 1922 | |||||||
| 17 | R. Abdul Jabbar R. Adipati Ario Kertoamoprojo |
1922 | 1934 | |||||||
| 18 | R. Adipati Abdul Aziz R. Adipati Ario Mangkuadiningrat |
1934 | 1942 | |||||||
| 19 | R. Zainal Fattah R. Tumenggung Notoadikusumo |
1942 | 1950 | 19 | ||||||
| 20 | R. Hairuddin Harjokusumo | 1951 | 1959 | 20 | — | |||||
| 21 | R. Moh. Hanafia | 1959 | 1960 | 21 | [Ket. 1] | |||||
| 22 | R. I. Abdul Rahem | 1960 | 1968 | 22 | ||||||
| 23 | Letkol CPM R. Haliudin |
1969 | 1974 | 23 | ||||||
| 24 | Letkol Moh. Tamyis |
1974 | 1976 | 24 | ||||||
| 25 | Letkol Inf Moh. Toha |
1976 | 1982 | 25 | ||||||
| 26 | H. Hadiatullah |
1983 | 1988 | 26 | ||||||
| 1988 | 1993 | 27 | ||||||||
| 27 | Drs. H. Subagio |
1993 | 1998 | 28 | ||||||
| 28 | Drs. H. Dwiatmo Hadiyanto M.Si. |
1998 | 2003 | 29 | ||||||
| 29 | Drs. H. Achmad Syafii Yasin M.Si. |
2003 | 2008 | 30 | Drs. H. Kadarisman Sastrodiwirjo M.Si. |
|||||
| 30 | Drs. KH. Kholilurrahman SH., M.Si. |
2008 | 2013 | 31 | ||||||
| (29) | Drs. H. Achmad Syafii Yasin M.Si. |
22 April 2018 | 14 Agustus 2017 | 32 | [Ket. 2] | Drs. H. Kholil Asy’ari |
||||
| — | Drs. H. Kholil Asy’ari |
14 Agustus 2017 | 5 Januari 2018 | [Ket. 3] | — | |||||
| 31 | 5 Januari 2018 | 22 April 2018 | [3] | |||||||
| — | Moh. Alwi (Pelaksana harian) |
22 April 2018 | 24 Mei 2018 | — | [4] | |||||
| — | Fattah Jasin (Penjabat) |
24 Mei 2018 | 24 September 2018 | [5] | ||||||
| 32 | H. Badrut Tamam S.Psi |
24 September 2018 | 24 September 2023 | 33 | Raja’e S.HI |
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