Diary of a Football Manager: Episode 1 – The Pentagon Challenge is helping me deal with FM 25 heartbreak

It was one of those moments where everyone remembers exactly what they were doing—the devastation, the disbelief, the thousands of lives ruined. No, I’m not talking about a real-world event, but the day when it was announced that Football Manager 2025 was delayed until March. Utter heartbreak.

After a moment of panic, I thought, “What am I going to do for the next few months?!” Going outside? Touching grass? Talking to my family? Absolutely not. So, I decided to embrace the ultimate challenge on Football Manager 2024 with a save to last me through the cold, rainy Manchester winter: the Pentagon Challenge.

For those unfamiliar, the Pentagon Challenge is notorious in the Football Manager community as one of the hardest challenges to complete. The goal? Win five major continental trophies, starting unemployed, with no coaching badges or experience. I need to secure victories in the Asian Champions League, the African Champions League, the CONCACAF Champions League, the Copa Libertadores, and finally, the biggest prize of all—the UEFA Champions League.

Simple, right? Not exactly. Let’s jump into how my save started off. 

The first step was to load up the key nations in each continent where clubs actually have a shot at winning their respective continental competitions. I’d have loved to include every country, but I didn’t want my MacBook to spontaneously combust. 

Job hunting began… and mistakes were made. I applied to nearly every club that would listen, resulting in a staggering 100 interview requests from teams in places like the Saudi Arabian 4th division. It genuinely took me about an hour to go through all of them. Eventually, I honed my focus: 1.5-star to 2-star teams were the sweet spot—clubs bad enough that they would give me a job, but not so low that they would have amateur players and train in car parks.  

I honed my focus: 1.5-star to 2-star teams were the sweet spot—clubs bad enough that they would give me a job, but not so low that they would have amateur players and train in car parks.  

After what felt like a lifetime of interviews and rejections, I finally landed a job. Welcome to the second tier of South African football with Black Leopards (what an incredible team name). The club, based in Thohoyandou, had been struggling ever since relegation from the top division in 2021. My mission: bring them back to the top division (and then probably jump ship at the earliest opportunity)

It quickly became clear that this wasn’t going to be easy. We were predicted to finish 11th out of 16 teams, and to make matters worse, the club was completely broke. Just before the season even kicked off, we were hit with a brutal injury crisis. I’m not sure if it was my training regime or if the players were made of glass, but I was running out of footballers.

Optimism still remained as we headed into the season opener against Orbit College, the worst team in the league. Surely, we could get the win. Well, it’s Football Manager, so you can guess what happened next. We took the lead, only to have an 86th-minute goal ruled out for offside, followed by Orbit scoring with their only shot on target in the 89th minute. Welcome back, I hadn’t missed this.

The struggles continued. Five matches in, and we had missed three penalties. Despite being top of the xG table, we had just one win and sat in a disappointing 8th place. I was coaching wins, trust me, but my players clearly weren’t on the same wavelength. 

At this point, you’re probably wondering what tactic I was using. Well, I didn’t reinvent the wheel. I stuck with a lopsided 4-2-3-1 formation. I needed to get wins on the board, so I wasn’t trying anything fancy. 

Eventually, the footballing gods smiled upon us, and our xG dominance began to translate into actual wins. Nine games in, we were only two points off the playoff spots. I switched to a 4-1-2-1-2, and things really started clicking. What you’ll soon learn about me is that I change tactics more than anyone on the planet. It’s rare I stick with the same formation for more than five games, even when we’re winning. Call me Pep Guardiola, but without the coaching badges or the trophies.

I didn’t reinvent the wheel. I stuck with a lopsided 4-2-3-1 formation. I needed to get wins on the board, so I wasn’t trying anything fancy.

At the halfway point in the season, we were sitting in third place, right in the playoff hunt. Our defence was still a mess, but thankfully, we were scoring goals. Largely thanks to one man: Andiswa Ndawonde. On paper, he didn’t look special—just a three-star rating and some pretty average stats. His stamina? Six. The man couldn’t run for more than 10 minutes without collapsing… but what a 10 minutes it was! He consistently bagged goals and assists, earning the highest average rating in the league.

This is just the beginning of my Pentagon Challenge. If you’ve been following my Twitter thread, you’ll recognize a lot of this story, but hopefully, it serves as a good recap of my journey so far. There’s plenty more to come as we move further along in the save, and trust me, things get crazy.

Stay tuned for more updates and follow my journey on X @Out of Context Football Manager