two digit year cutoff

-- show settings:

EXEC sp_configure 'two digit year cutoff'

GO

-- two digit year cutoff configuration:

EXEC sys.sp_configure N'two digit year cutoff', N'2030'

GO

RECONFIGURE WITH OVERRIDE

GO

-- or In Object Explorer, in the server Properties

By default, SQL Server interprets two-digit years based on a cutoff year of 2049:

SELECT CAST('02/02/02' AS DATETIME), 

CAST('02/02/49' AS DATETIME),

CAST('02/02/50' AS DATETIME)

-- output:  2002-02-02,2049-02-02,1950-02-02

Specifying four-digit years is Always recommended.