Check your schematic and find the horizontally-oriented circuit that leads to the 1000-pt relay (likely the L relay?). It should include a normally open (NO) switch on the 100-pt relay (M relay?), along with a NO switch labelled 9th-position, 2nd hundreds. There may be another switch in the circuit that would need to be checked.
Then, if the 1000-pt relay is indeed pulling in when the 2nd-player hundreds reel advances from 9 to 0, there will be another NO switch on the thousand-point relay that needs to conduct to fire the "add 2nd thousands unit" solenoid (circuit found lower down on the schematic).
Keep in mind that the bane of EM troubleshooting is the switch that "appears" to be clean and closed, but still does not conduct electricity. I've run into that situation many times. Some folks use alligator clips and jumper wires to short circuit each switch to make sure that isn't happening.