I think this is the code you need:
DROP TABLE IF EXISTS #TEST;
CREATE TABLE #TEST (
KEY1 integer NOT NULL,
Dt date NOT NULL,
ISSUE integer NOT NULL,
);
INSERT #TEST
(KEY1, Dt, ISSUE)
VALUES
(100, CONVERT(date, '9/01/2010', 103), 5),
(100, CONVERT(date, '14/01/2010', 103), 10),
(100, CONVERT(date, '13/01/2010', 103), 9),
(101, CONVERT(date, '08/01/2010', 103), 12),
(101, CONVERT(date, '25/01/2010', 103), 23),
(101, CONVERT(date, '01/01/2010', 103), 3),
(101, CONVERT(date, '20/01/2010', 103), 22);
SELECT
W.KEY1, DIFF = W.ISSUE - W.prev
FROM
(
SELECT
T.*,
rn = ROW_NUMBER() OVER (
PARTITION BY T.KEY1
ORDER BY T.Dt DESC),
prev = ISNULL(LAST_VALUE(T.ISSUE) OVER (
PARTITION BY T.KEY1
ORDER BY T.Dt DESC
ROWS BETWEEN CURRENT ROW AND 1 FOLLOWING), 0)
FROM #TEST AS T
) AS W
WHERE
W.rn = 1;
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