The first year of obtaining Singapore PR status starts from the date of SPR conversion. This refers to the date indicated on the entry permit (Form 5 or Form 5A) issued by the Immigrations and Checkpoints Authority of Singapore (ICA). It ends on the last day of the month of the first anniversary of SPR conversion.

The second year of obtaining SPR status starts from the first day of the month after the month of the first anniversary of SPR conversion. It ends on the last day of the month of the second anniversary of SPR conversion.

For example, if your employee obtained SPR status on 21 October 2018, the start and end dates will look like this: 

First Year
Start: 21 October 2018
End: 31 October 2019

Second Year
Start: 1 November 2019
End: 31 October 2020

Third Year
Start: 1 November 2020
End: N/A

For further info, you can refer to CPF website. Just scroll down until you see "How do I determine the year of SPR status for my SPR employees?" 😎