Hi Colin,

It's quite easy to go mad trying to do this sort of thing in T-SQL today (future things like ordered aggregates might help, I don't know).

A cursor solution is straightforward, the only downside being that T-SQL cursors suck performance-wise. So, I would use a CLR cursor: the obvious procedural logic in a CLR stored procedure that reads from Schedules and Requests and returns matched output as a set that can be directly INSERT...EXEC'd into the Scheduled Requests table. If the output set is huge, you could even use bulk copy from the CLR code.