...aaaaand too late to edit my post... so a new one...
Something seems to happen, but I don't know why or what:
[23:33:38] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Last Step&track=Seafoam Green&limit=200&format=json&page=1
[23:33:38] Found 0 scrobbles in last.fm of "Seafoam Green"
[23:35:37] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Céline Dion&track=Because You Loved Me&limit=200&format=json&page=1
[23:35:38] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Helen Merrill&track=My Favorite Things&limit=200&format=json&page=1
[23:35:38] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Clarke-Boland Big Band&track=My Favorite Things&limit=200&format=json&page=1
[23:35:38] Found 0 scrobbles in last.fm of "Because You Loved Me"
[23:35:38] Found 0 scrobbles in last.fm of "Summertime"
[23:35:38] Found 0 scrobbles in last.fm of "My Favorite Things"
[23:35:39] Found 0 scrobbles in last.fm of "My Favorite Things"
[23:35:39] Found 0 scrobbles in last.fm of "Summertime"
[23:35:39] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Janis Joplin&track=Summertime&limit=200&format=json&page=1
[23:35:40] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Ike Quebec&track=Nature Boy&limit=200&format=json&page=1
[23:35:40] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Miles Davis&track=Milestones&limit=200&format=json&page=1
[23:35:40] Found 0 scrobbles in last.fm of "Summertime"
[23:35:40] Found 0 scrobbles in last.fm of "Nature Boy"
[23:35:40] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=George Gershwin&track=Summertime&limit=200&format=json&page=1
[23:35:41] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Delegation&track=Put a little love on me&limit=200&format=json&page=1
[23:35:41] Found 0 scrobbles in last.fm of "Milestones"
[23:35:41] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Röyksopp&track=What Else Is There?&limit=200&format=json&page=1
[23:35:41] Found 0 scrobbles in last.fm of "Summertime"
[23:35:42] Found 0 scrobbles in last.fm of "What Else Is There?"
[23:35:42] Found 0 scrobbles in last.fm of "Put a little love on me"
The first song (Seafoam Green) was played during my test, all other songs weren't played the last months, nor have I clicked on them in f2k or any other player.
I have seen this:
[23:28:10] Starting to pull legacy scrobbles (before 1531568361)
[23:28:10] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getRecentTracks&api_key=mykey&user=myuser&limit=200&format=json&to=1531568361&page=1
[23:28:10] Track scanned in 940.969 ms
[23:28:13] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getRecentTracks&api_key=mykey&user=myuser&limit=200&format=json&to=1531568361&page=2
[23:28:14] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getRecentTracks&api_key=mykey&user=myuser&limit=200&format=json&to=1531568361&page=3
[23:28:15] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Ceephax Acid Crew&track=Trabzonspor&limit=200&format=json&page=1
[23:28:16] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getRecentTracks&api_key=mykey&user=myuser&limit=200&format=json&to=1531568361&page=4
[23:28:16] Found 0 scrobbles in last.fm of "Trabzonspor"
[23:28:18] Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getRecentTracks&api_key=mykey&user=myuser&limit=200&format=json&to=1531568361&page=5
But the pull date still is stuck on the same date 2018-07-14 13:39:21 as in my first post. (see screenshot)
And, after playing the song as you described, this is the result:
Querying last.fm: http://ws.audioscrobbler.com/2.0/?method=user.getTrackScrobbles&api_key=mykey&user=myuser&artist=Bebe Rexha&track=Bad Bitch&limit=200&format=json&page=1
Found 0 scrobbles in last.fm (since last known scrobble at 2018-06-22 12:28:02) of "Bad Bitch"
Please, if you provide a version with detailed debug information, make it save those infos to disk and not only log to console. I have too much other components writing to the console and its hard to separate the important lines from the useless ones ;-}
The last.fm screenshot contains music by daft punk, which was played simultaneously from iTunes, you can ignore it. All other songs are played via f2k like the playlist I screenshotted in my post above.