What is the best method to reissue a stale cheque to a supplier if cheque was dated from previous year end period?

Hello MCCM, 

Welcome to the Community page, 

You can change the date, so that, that entry will be posted on the date that you would like to keep in track with it. 

@MCCM 

Record a deposit for the amount of the stale check into the checking account and assign it to a temporary clearing bank account (set one up if you don't have one).  Then, write the new check and assign it to the same clearing account as the deposit you just created.  This keeps the stale check in the closed period and the new deposit/check will net to zero in the current period. 

When you reconcile the bank account, clear the stale check with the new deposit and clear the new check when it clears.