It is easiest if you have a numbers table. If you don't have one, create one like shown below and then use it like shown in the second query.
-- create numbers table
CREATE TABLE #Numbers(n INT NOT NULL PRIMARY KEY);
;WITH cte(n) AS (SELECT 1 UNION ALL SELECT n+1 FROM cte WHERE n < 5000)
INSERT INTO #Numbers SELECT n FROM cte OPTION (MAXRECURSION 0);
INSERT INTO Bookings2(PitchType_Skey)
ORDER BY n;
-- get rid of numbers table
DROP table #NumbersIf you don't have permissions to create temp tables, you could use a cte approach - if that is the case, please reply back.