At first glance your original attempt seems pretty close. I'm assuming that clockDate is a DateTime fields so try this:
IF (NOT EXISTS(SELECT * FROM Clock WHERE cast(clockDate as date) = '08/10/2012')
AND userName = 'test')
BEGIN
INSERT INTO Clock(clockDate, userName, breakOut)
VALUES(GetDate(), 'test', GetDate())
END
ELSE
BEGIN
UPDATE Clock
SET breakOut = GetDate()
WHERE Cast(clockDate AS Date) = '08/10/2012' AND userName = 'test'
END
Note that getdate gives you the current date. If you are trying to compare to a date (without the time) you need to cast or the time element will cause the compare to fail.
If clockDate is NOT datetime field (just date), then the SQL engine will do it for you - no need to cast on a set/insert statement.
IF (NOT EXISTS(SELECT * FROM Clock WHERE clockDate = '08/10/2012')
AND userName = 'test')
BEGIN
INSERT INTO Clock(clockDate, userName, breakOut)
VALUES(GetDate(), 'test', GetDate())
END
ELSE
BEGIN
UPDATE Clock
SET breakOut = GetDate()
WHERE clockDate = '08/10/2012' AND userName = 'test'
END
As others have pointed out, the merge statement is another way to tackle this same logic. However, in some cases, especially with large data sets, the merge statement can be prohibitively slow, causing a lot of tran log activity. So knowing how to logic it out as shown above is still a valid technique.