Вам не нужно регулярное выражение.Укажите тип данных:
import pandas as pd
dates = ["04/20/2009", "04/20/09", "4/20/09","4/3/09","6/2008","12/2009","2009","2010"]
df = pd.Series(dates,dtype='datetime64[ns]')
print(df)
Вывод:
0 2009-04-20
1 2009-04-20
2 2009-04-20
3 2009-04-03
4 2008-06-01
5 2009-12-01
6 2009-01-01
7 2010-01-01
dtype: datetime64[ns]