Well, you don't say much about your setup on the Midi Raider, which would help to "debug" your problem… Anyways:
– Maybe the presets are saved as active on the H9 and Timeline? In this case you should save them as bypassed and have the Midi Raider activate them when needed.
– On the Raider manual it says: • A MOMENTARY switch type sends the “on” control value when the switch is pressed, turning the L.E.D. on, and the “off” control when the switch is released (the L.E.D. remains on). The L.E.D. changes status once each time the switch is pressed and released. When changing presets, if the new switch status is different than the current status, the “on” value is sent followed by the “off” value 5 milliseconds later. The MIDI control change that is associated with this switch is sent only if the switch status changes.
… that could be the cause of your problem too.