I tried a little bit on solution and got it right :w00t:

So here is the code

SELECT t.UserName, t.Drink, t.CreatedDate, x.Value

FROM #TEMP t

OUTER APPLY (

SELECT TOP 1 Value

FROM

(

--SELECT * FROM #TEMP

SELECT TOP 2 Value , CreatedDate

FROM #TEMP TI

WHERE TI.UserName = T.UserName

AND TI.CreatedDate < T.CreatedDate

--AND TI.Drink IN ('HardDrink')

ORDER BY TI.CreatedDate DESC

) T

ORDER BY CreatedDate DESC

) x

WHERE t.Drink IN ('HardDrink')