Custom music looping! [SOLVED]

Hmm, let's try...

I have a VLC and empty playlist. I also have three files for one track.
Thirst track is the intro with rest of the track but without the fadeout
Second track is everything but intro, with the fadeout mixed with in beginning of it and not in the end

I place them in the playlist like that:
1. First
2. Second
3. Second
4. Second
... etc.

If VLC can play them seamlessly, you would (most likely) hear what I'am aiming for in the game.

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As for now the tracks are being looped from end to start. Once the track reaches it's end, it is immidietly started again from the beginning.

But what I asking for is a bit more complicated.

I don't mean two different tracks to be mixed - just two instances of the one, same track.
It is all to avoid the "moment of silece" which is a seam in looping. A smooth seam, but still.
Additionally I want the intro of the track to be played just once - at the beginning of the match. This will also give the musitians (like me) posiibility to make the music warm up the match with intro stage

Someone who was playing with trackers might know what am I aiming for. It is very similiar, but requires also mixing the track's fadeout with the beginning of it's new instance to avoid the CUT effect.