1999
The total number of registered voters in the state was 1,496,058. Total number of votes cast was 547,077, while number of valid votes was 536,252. Rejected votes were 10,825.
| Candidate | Party | Votes | % | |
| Adebisi Akande | Alliance for Democracy | 295,557 | 68.47 | |
| All People’s Party | 136,105 | 31.53 | ||
| Total | 431,662 | 100.00 | ||
| Valid votes | 431,662 | 97.55 | ||
| Invalid/blank votes | 10,825 | 2.45 | ||
| Total votes | 442,487 | 100.00 | ||
| Registered voters/turnout | 1,496,058 | 29.58 | ||
2003
A total of three candidates registered with the Independent National Electoral Commission to contest in the election. PDP candidate Olagunsoye Oyinlola won election for a first tenure, defeating AD Incumbent Governor, Adebisi Akande, and ANPP’s Lai Oriowo.
The total number of registered voters in the state was 1,367,627. However, only 58.63% (i.e. 801,812) of registered voters participated in the excerise.
| Candidate | Party | Votes | % | |
| Olagunsoye Oyinlola | People’s Democratic Party (PDP) | 493,509 | 67.55 | |
| Adebisi Akande | Alliance for Democracy (AD) | 237,041 | 32.45 | |
| Lai Oriowo | All Nigeria Peoples Party (ANPP) | |||
| Total | 730,550 | 100.00 | ||
| Registered voters/turnout | 1,367,627 | – | ||
2007
Olagunsoye Oyinlola from the People’s Democratic Party won the election, defeating Rauf Aregbesola from the Action Congress of Nigeria. Registered voters was 1,297,297.
| 2007 Osun State gubernatorial election | |||||
| Party | Candidate | Votes | % | ±% | |
| PDP | Olagunsoye Oyinlola | 426,669 | 0 | ||
| ACN | Rauf Aregbesola | 240,722 | 0 | ||
| PDP hold | |||||
2014
A total number of 20 candidates registered with the Independent National Electoral Commission to contest in the election.
A total number of 1,407,222 voters registered in the election.
| Candidate | Party | Votes | % | |
| Rauf Aregbesola | All Progressives Congress | 394,684 | 56.68 | |
| Iyiola Omisore | People’s Democratic Party | 292,747 | 42.04 | |
| Labour Party | 8,898 | 1.28 | ||
| Total | 696,329 | 100.00 | ||
| Registered voters/turnout | 1,407,222 | – | ||
2018
The rerun on 27 September was called after the first round was declared inconclusive, on account of Ademola’s margin of victory being smaller than the number of cancelled votes in seven polling units
Rerun Election
| Candidate | Party | Votes | % | |
| Gboyega Oyetola | All Progressives Congress | 255,505 | 36.71 | |
| Ademola Adeleke | People’s Democratic Party | 255,023 | 36.64 | |
| Iyiola Omisore | Social Democratic Party | 128,053 | 18.40 | |
| Moshood Adeoti | Action Democratic Party | 49,745 | 7.15 | |
| Fatai Akinade Akinbade | African Democratic Congress | 7,681 | 1.10 | |
| Total | 696,007 | 100.00 | ||
| Registered voters/turnout | 696,007 | – | ||
2022
Results
Candidates’ vote share
Ademola Adeleke (PDP) (50.14%)
Gboyega Oyetola (APC) (46.62%)
Other candidates (3.24%)
| 2022 Osun State gubernatorial election | ||||
| Party | Candidate | Votes | % | |
| PDP | Ademola Adeleke | 403,371 | 50.14% | |
| APC | Gboyega Oyetola | 375,027 | 46.62% | |
| ADP | Kehinde Munirudeen Atanda | 10,104 | 1.26% | |
| A | Akin Ogunbiyi | 4,514 | 0.56% | |
| LP | Yusuf Sulaimon Lasun | 2,729 | 0.34% | |
| AAC | Peter Segun Awojide | 2,148 | 0.27% | |
| YPP | Ademola Bayonle Adeseye | 1,303 | 0.16% | |
| APM | Awoyemi Oluwatayo Lukuman | 1,222 | 0.15% | |
| PRP | Busuyi Ayowole | 1,007 | 0.13% | |
| NRM | Samuel Adetona Abede | 777 | 0.10% | |
| APP | Adebayo Adeolu Elisha | 601 | 0.07% | |
| SDP | Akinrinola Oyegoke Omigbodun | 515 | 0.06% | |
| New Nigeria Peoples Party | Rasaq Oyelami Saliu | 393 | 0.05% | |
| BP | Adeleke Adedapo | 374 | 0.05% | |
| ZLP | John Olufemi Adesuyi | 364 | 0.05% | |
| Total votes | 804,450 | 100.0% | ||
| Invalid or blank votes | 18,674 | N/A | ||
| Turnout | 823,124 | 42.16%[a] | ||
| PDP gain from APC | ||||