OK, boredom set in the other day and I had a game on holiday overnight. I'm now up to July 2024. What's happened in the past 15 years?
The Big Four
Arsenal had a nasty reputation in FM09 for being overpowered. This time they're not...in 15 years they've won the Premiership 3 times (2015, 2018 and 2021), and have been second or third a further 8 times. The Champions League still eludes them, but they won the Europa League in 2024. They've also won the FA Cup six times and League Cup twice. The only two players I can see who have been in the team from the beginning are 37-year-old Cesc Fabregas and 34-year-old Kieran Gibbs. Tony Mowbray is now manager, earning £185,000 a week

And despite the home-grown rule introduced in 2010 and Wenger leaving in 2012, Arsenal is STILL loaded with foreigners. Gibbs and only two others out of twenty-nine in the senior squad are English. The other HG players: 3 Spanish, 2 German, 2 Brazilian, 1 Italian, 1 Argentinian. They've got a few familiar names in the back room - in addition to Tony Mowbray, real-life Man Utd youth coach Paul McGuinness and Man Utd player Michael Owen are both 1st team coaches at Arsenal, while Stephen Ireland is a youth coach, and Oliver Bierhoff is a scout.
Arsenal's power has been toned down, but Chelsea have been running riot. In 15 years they've won the Premiership no fewer than 10 times, and finished second 4 of the other 5 years. In 2011, the only year they didn't finish first or second, they came fourth. They've won the Champions League twice and been runner up thrice. Won the FA Cup five times and the League Cup five times. I don't see anyone in the squad who started the game at the club, but a couple of former Man Utd players are there (Ben Amos is in the senior squad, and Matt James is in the reserves). As with Arsenal, they've only got three Englishmen in their senior squad, with the other HG spots filled with 2 Spanish, 1 German, 1 Italian, 1 Belgian, 1 Hungarian and 1 Argentinian player. They now play at the horribly titled Zola Arena, where they moved in 2014, and its capacity was upgraded to 65,000 in 2021. They've had a few managers, all of whom you should be familiar with - Carlo Ancelotti left in 2015 and was replaced by Juande Ramos. Ramos retired in 2018 and was replaced by current manager Josep Guardiola. Nani is employed as a scout for Chelsea
Liverpool have struggled quite a lot. Not only have they still not won the Premiership (over 3 decades without winning the top flight of English football), in 15 years they've finished second or third a miserable four times. Their traditional "poor" performance in the league but dominance in Europe and in cups hasn't been reflected in the game - only a single Europa League title to their name, they've not won the FA Cup at all and they've only won the League Cup once. Nobody from the current Liverpool squad started the game at the club. The only name I recognise is Philipp Prosenik in the reserves (he starts in the Chelsea U18s, IIRC). So, they've gone fifteen years with virtually no trophies, and as you may well expect, they've had quite a few managers. Rafa was sacked in 2011. Marco van Basten took charge. van Basten left to manage AC Milan in 2014 and he was replaced by Harry Redknapp. Harry retired in 2016 and was replaced by Vicente Del Bosque, who himself retired in 2017. Phil Brown has been in charge since, in his first managerial position since getting sacked from Hull in 2013 when they were relegated from the Premiership

Other noteworthy staff...real-life Celtic coach/assistant/whatever Mark Venus is Phil Brown's assistant, and real-life Rangers assistant Ally McCoist is a coach.
Liverpool have been very poor, and Man Utd haven't exactly been much better, Danny Welbeck the sole survivor of a team who'd seen better days. Haven't won the Premiership, but have a reasonable record of finishing in the top three. Won the Champions League twice, won the FA Cup twice and won the League Cup thrice. After Alex Ferguson retired in 2012, Javier Aguirre became manager, and was rather loyal - he was manager up until he was sacked in 2021 after a 3-0 loss to Inter Milan that guaranteed they'd finish bottom of their CL group. After his sacking, they've since had real-life Huddersfield manager Lee Clark in charge. The backroom staff doesn't appear to have changed
too much over the years - many of the names are ones I know very well from my playthroughs with United. Matty Fryatt, Stiliyan Petrov and Bjorn Helge Riise are all employed by the club as scouts, but there's not much to talk about here, in truth. One other thing I found rather interesting, but also rather odd: after David Gill left the club in 2020, Sir Bobby Charlton took over as chairman of the club...but he only remained in charge for a month and a half...which I think is even less time than Al-Fahim was owner of Portsmouth
The Other Premiership Teams
If you kept count above, you'd have noticed that the big four's dominance of the Premiership had gone down the toilet - if you could get past Chelsea, odds were that you'd win the title. Arsenal only managed this three time. The others were Man City in 2011 (rubbing it in Man Utd's faces) and Everton in 2019 (rubbing it in Liverpool's faces)

Man City still have bags of money and the ability to pretty much write a blank cheque when the transfer market opens, but around £835m spent on players has translated to only three trophies - Premiership in 2011, League Cup in 2011 and FA Cup in 2019.
Anyway, the vast majority of the teams in the 2009/10 Premiership season are still in the Premiership to begin 2024/25. The scant few who are missing are Hull and Portsmouth who were both relegated in 2024, Birmingham who were last relegated in 2022, Burnley who were last relegated in 2021, and Stoke who have plummeted down - they dropped out of the Premiership in 2015, spent three years in the Championship and have been yo-yoing between League 1 and League 2 (they're currently in League 1) for the past six years.
Of the fifteen remaining clubs, you know that Chelsea have never finished lower than fourth and therefore have never been relegated. None of the top four have been relegated...and other teams to stay in the Premiership every year are Aston Villa, Everton, Fulham (even though one year they were never higher than 14th

), Man City, Sunderland, Tottenham and West Ham.
So 15 years on, 15 teams are still in the Premiership and 11 of those have never left the Premiership.
Premiership Newbies
Anyone who's played a few long-term games in FM09 will probably be surprised to hear that Leeds have still never returned to the Premiership in this game. The five teams to have been promoted to the Premiership are Leicester (this is their first season), Middlesbrough (stayed up since 2013), Newcastle (been up and down a few times - this is their second consecutive season right now), Nottingham Forest (they've been up and down a lot as well, and this is also their second consecutive season) and West Brom (again, up and down a few times, but this is their sixth consecutive season now)
Other teams to have been up at some point are Bristol City, Sheffield United, QPR, Swansea and Peterborough.
Scotland
Old Firm domination is still very much in place. Hearts have won once and have quite solidly made their mark as the third team in Scotland, but otherwise the SPL has been won by Rangers (10 times) or Celtic (4 times) every year.
Europe
Not exactly seeing any signs of total dominance by any single team or nation, though Juventus have won the Champions League five times and been runner-up twice more. Other winners: Man Utd and Chelsea from England (twice each), Inter Milan from Italy (once) and Real Madrid (once), Barcelona (twice) and Atletico Madrid (twice) from Spain. All runners-up have been from those nations as well (many of them being those named sides, actually), except for Bayern Munich in 2010.
The Europa League's more open. Fifteen years, and fifteen different winners. Palermo, Genoa and Galatasaray have all been runners-up twice but haven't won it. Inter are the only other team to have appeared in two finals, winning one, losing one.
International Level
World Cup winners: Brazil, Brazil, Argentina, Spain
The 2014 final would have been good to watch. Pato scored for Brazil in the 17th minute. Chiellini equalised in the 54th minute, and Balotelli took Italy ahead in the 68th minute. Hulk FINALLY eked out an equaliser in the 86th minute, taking the game into extra time. Italy then totally collapsed. Breno scored in the 105th minute, Kaka got one in the 110th, and Hulk got a second to end the game 5-2 in the 120th minute.
European Championships winners: Greece, Spain, France, Germany
The FIFA top ten: Spain, England, Croatia, France, Brazil, Italy, Germany, Holland, Portugal, Mexico.
Other British/Irish nations: Scotland are 28th, Republic of Ireland are 50th, Wales are 51st and Northern Ireland are 52nd.