FM08, I got to around 2031 and then the game wouldn't allow me to play on.
I started as Liverpool, and got the sack around the 2014 season, and took charge of the Irish national team for the World Cup. Interestingly enough, I got to the semi-finals of the 2014 WC and after being in charge for about three months, they sacked me after one loss to Greece. Never been sacked by a national team until then.
I believe I skipped one whole season on holiday LOL And then came back around the 2016 season and took charge of Everton for awhile.
Came second one season with Everton, around the 2018 season and then they sacked me for not meeting expectations. Liverpool had been relegated to the Championship so I returned, and some won't believe this, but Steven Gerrard was still going! He was like 40 and had nothing but good finishing, set-pieces, mentality skills and so on but I still played him until he retired.
Got Liverpool back up and managed them until I went to Man United and won the Prem three seasons in a row.
After that the game just wouldn't enter the new season. I tried everything, but it wouldn't budge so I left it, never even bought FM09. I miss that game