I know this doesn't count as I started with Annagh in the first season, but thought I'd mention it anyway.
Got to the top league, and struggled there for a while. Came 2nd 4 times in a row, but crept closer to Linfield each time. Then in my 7th season in the top league everything clicked. Didn't lose a game, and won 29, with 105-3 goal-difference. Strange stuff!
Got to the group stage in the UEFA Cup in the 5th try, where we finished 4th of 5, but did quite well.
This season I for the first time played the CL, and have done good so far. Miraculously managed to beat Lille in the 3rd qualifier round, and got the group stages on first try. Have so far lost 4-1 away (deserved almost draw) to Sporting, and just drew Chelskij 2-2(!!). The latter with a heap of luck.
Just shows that it is actually possible to go places even in the smaller leagues, and I'm playing with LLM rules.
We're 191st in the ranks this season. But will skip up quite a few as we managed the group stage of CL this year.
Club Honours - Annagh Utd 2014/15