9.1 – Bonehead’s Bank Holiday

Welcome back to my Pentagon Challenge. Season 9 and Cape Town City FC take on the 2023/24 season as Champions of South Africa.

Episodes: 1.1, 2.1, 2.2, 3.1, 3.2, 4.1, 4.2, 5.1, 6.1, 6.2, 6.2, 6.3, 7.1, 8.1, 8.2

Its my second full season in charge of CTCFC and I’m expecting great things from this campaign.

We finished with a 16 game unbeaten run to end the previous season so I think with the new signings, we can kick on and retain the title with a decent shot at the African Champions League. As South Africa is the only playable league on the continent, and we won the league by 13 points, I fancy my chances to close off the second prong of the Pentagon Challenge.

Whats very odd about the African Champions League is that it doesn’t sit in line with the South African Premier League. This basically means that although we’ve qualified, our Preliminary Round games won’t kick off until February 2024, halfway through the league season. The first six months are basically a holiday.

So let’s crack on with the league campaign, and retaining my first domestic title.


Six really decent signings are brought in.  Three, Ouattara, Amamoo and Zwane are for the future, with the others ready to slot into first team football. Minimal outlay for them all means there is also minimal risk to the club. I like to leave a legacy.

First up in South Africa is always the Super 8 Cup. The top eight teams from last season compete for the cup before November.

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The defending champions win again! Bill Shankly picks up his sixth career trophy with another win against the old rivals Ajax CT in extra time. They must hate me.


The first half of the season in the league starts off as we ended 2022/23 with three high scoring wins.

The next twelve games to take us to the halfway point in the seasons end in W10-D1-L1 to keep the domination of the Premiership table.

Ajax CT did get their revenge on me though, by beating me in the SA Knockout Cup final 1-0. Pretty annoying as I dominated the game and missed a hat-full of chances.


Please join me next time for part two of the season. Coming soon.



Thanks for reading. @AjaxU19s


8.2 – Force of Nature

Welcome back to my Pentagon Challenge. Bill Shankly is in charge of his 3rd team of the Pentagon Challenge. Season 2022/23 in Cape Town and its mid-season break time, January 2023.

Episodes: 1.1, 2.1, 2.2, 3.1, 3.2, 4.1, 4.2, 5.1, 6.1, 6.2, 6.3, 7.1, 8.1

So left you in 8.1, top of the table after nine games. A great start and a seven game winning run that ended straight away with a 2-2 draw against SuperSport Utd. Three wins and a draw from the next five games took us into the winter break in a great spot atop of the South African Premiership.

After this great start in South Africa, the national team came calling.

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Sorry chaps, I’m not taking it – Cape Town need full concentration.


So in January 2023, after a superb start (W10-D3-L2) I have the second half of the season to secure the African Champions League qualification.

Time to go on a run.

Twelve wins and three draws in the final half of the season and I smash the division by 13 points from rivals Ajax Cape Town. Champions League qualification is ours! I did lose in the SA Knockout Cup somewhere along the way though.


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I was still in the South African Cup, with a second final beckoning vs SuperSport. On for the treble. Now this is luck:

SuperSport Utd v Cape Town City_ Overview Overview

A very close game, in which you could say I deserved to lose. In extra time, their boy Mayo missed a penalty, and then he also bottled it in the shootout.

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So a ridiculously successful first full season in Africa, securing the domestic treble and qualification to the continental tournament I need next for the Pentagon.

Cape Town City Football Club_ Senior Fixtures

Full League Season Results



Join me next episode continuing my journey with Cape Town City into 2023/24.

Thanks for reading. @AjaxU19s

8.1 – Full On

Welcome back to my Pentagon Challenge. One ACL Cup win down. Season 2022/23 begins in Cape Town – my first full season at the club.

Episodes: 1.1, 2.1, 2.2, 3.1, 3.2, 4.1, 4.2, 5.1, 6.1, 6.2, 6.3, 7.1

A respectable 8th after six months at CTCFC last season and time to put a Shankly sized stamp on the team.

Straight into the transfers. I knew we had some good players from last term, but they could so easily be improved. Limitations on foreign players are a maximum of three, so the scouts had been given the last six months scouting the local area and had unearthed a few boys I wanted to bring into the squad.


Mashishi, Percy Kunene and Jones looked like future gems.

As the league season kicked off, in South Africa, the top eight teams from last year compete in the Super 8 Cup – very early on in the season. I’d been drawn against local rivals Ajax who were suitably dispatched 1-0 before I destroyed Orlando Pirates (best kit ever in real life 2017 by the way) 4-0.

A final was set versus my new foes, Kaizer Chiefs. I’d lost to them last time around in the SA Cup final so I asked the players for immediate revenge.

We got it, winning comfortably 3-1 with Kunene, my new summer signing closing the game out in the 83rd minute. My first trophy, by October, in South Africa and third overall for Bill Shankly – great for the reputation!


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South African Super Eight Cup_ Overview Stages

Nine games had elapsed in the league campaign, nearly 1/3rd of the way through and after an awful start, losing vs Ajax and drawing with the Sundowners, I am on a seven game winning streak. Goals from everywhere is helping this as I’m regularly scoring three or four a game – usually in the first half which is killing teams.



Top of the table after nine, with a game in hand.

Join me next time for the rest of the season.

Thanks for reading. @AjaxU19s

7.1 – A Quick Peep

Welcome back. 2021 ended with Bill Shankly’s Chongqing lifting the Asian Champions League trophy, step one on this immensely interesting Pentagon Challenge. Check out the previous episodes below.

Episodes: 1.1, 2.1, 2.2, 3.1, 3.2, 4.1, 4.2, 5.1, 6.1, 6.2, 6.3

Looking back, it’s taken two seasons to build the squad needed to compete in the league, one to gain entry to the ACL and then one to win the ultimate continental trophy. I’m still short a league title but for this challenge, who cares!?


Life so far, just the two manager of the month awards!


Now my time with Chongqing comes to a natural end – where to next?

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2021 ticked into 2022, and after I got over my New Year’s Eve hangover, I decided to scout South Africa for jobs. Only a couple were on offer – Baroka FC and Cape Town City FC. Neither looked to have a decent reputation, but CTCFC did offer a 64,100 seater stadium, as well as, well, being in Cape Town. Who can turn down that beautiful spot?

After a quick formal interview where – as I mentioned in 1.1 – I basically just ask for nothing and agree to everything, CTCFC offer me the role.

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Well they would have, had Chongqing not asked for a massive payoff, so I have to ask them to drop their price. Two pieces of silverware meant they were very honest, and let me go.

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Into the Cape Town City hot seat. It’s a beautiful area of the world and Bill is excited to try out the wineries in the area on his days off.



I land in Cape Town halfway through the season, with the boy sitting in 12th from 16 teams. Their record is W4-D4-L7 and that leaves us with just 16 points from the 15 games.


I bring in a couple of players, including Mopedi (Jan) & Mfodolofo (March) as the window in SA seems to be open for a few months which is great news. My standard process of improving the backroom as much as possible with better coaches and scouts gets underway straight away, and the CTCFC even allow me to expand the coaching team – something I’m always doing at every club – key to improving the young potential stars.

We start the Shankly era in true style, winning the opening two games. The next eight games sees CTCFC pick up 13 points from an available 24, taking us up to 8th with 35 points.


A hit and miss last five games sees just one win and two draws.  I only score one goal which is a concern I’ll need to address going into the next transfer window. We finish a respectable 8th.

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The South African Cup run is something to be proud of though. A great few results in the rounds, beating a very strong Wits team, as well as massive Cape Town rivals Ajax in the semi-finals took me all the way to the FNB Stadium!

Lucky Khoza nudges us ahead after just two minutes before the Kaizer Chiefs pull one back just on half time. The game peters out and goes to penalties. We lose.

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Not bad for the first six-months though, and a good showing from the mainly inherited squad.

Join me for the next part as we jump into pre-season and a first transfer window for Bill Shankly in Africa.

Thanks for reading. @AjaxU19s

6.3 – Pass Me Down The Wine

Welcome back to my Pentagon Challenge.  The end of 2021 and Shankly has guided Chongqing of the Chinese Super League to its first Asian Champions League Final.

Episodes: 1.1, 2.1, 2.2, 3.1, 3.2, 4.1, 4.2, 5.1, 6.1, 6.2

As I mentioned in episode 6.2 the league petered out and I finished a very respectable 3rd place, one eye on the main event – the final of the Asian Champions League.


My first taste of continental football on this challenge and I’d made the final. Delighted with my success domestically in China though I am – we’re only here for one thing. We’d had a very solid couple of seasons and this momentum was proving useful in the ACL.

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The big one

I’ve drawn the Saudi Arabian League’s best team, Al-Hilal. They are the current runners up of the Asian Champions League – in fact they have been the bridesmaid for the past three years!

Asian Champions League_ History Past Winners

The first leg, over in the KSA gets off to a great start. Tan Long slotting home in the 13th minute. We are holding on nicely until deep into the second half, when Argentinian striker Lucas Alario notches goal twelve and thirteen of his continental campaign in six horrible minutes.

I go to attacking, and Mr Jinx steps up to finish a team move to keep us in the tie. Taking a 2-2 draw to the Congqing Stadium would be beautiful.

Then we conceed again in the 90th minute. Disaster. 3-2.

Chongqing Lifan_ Schedule Senior Squad

I need a solid home win now, and a full 57,000 crowd are going to be needed to push the boys over the line for my first trophy in this Pentagon Challenge.

Half time – 0-0.

Then. Up steps veteran centre-back Jung Woo-Young, a man I’d inherited, to leap highest and nod in a corner in the 52nd minute. Time to hold on.

Thats it! The first Champions League trophy of this campaign! Woo-Young takes the MOM award and we have stolen the win on away-goals! Massive.

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Absolutely delighted.


We can’t leave Chongqing quite yet, as the FA Cup final is still to come versus none other than League Champions Huaxia Xingfu in another two legged affair.

Before the Champions League Final second leg, I’d secured a 1-1 draw with Xingfu at home. A 2-2 draw away from home is enough to take my second trophy in four days.

Chinese FA Cup_ Matches Fixtures & Results


Double trouble.

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Still in the Club World Championship we draw Brazilian side Santos (SAN). I surely can’t resign yet with another bit of silverware on offer?

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The less said the better. Lost 1-0 to Santos after a penalty just 2 minutes into the game, before then losing the third place playoff to Kaizer Chiefs of all people.

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So finally, we complete part one of the Pentagon Challenge.

One and a half years at Xiangtao, jumping ship to Chongqing, where it took 3 years to qualify for, and one year to win the Asian Champions League.


Join me next time to find out what lies in wait for Bill Shankly next.

Thanks for reading. @AjaxU19s

6.2 – Up In The Sky

Welcome back to my Pentagon Challenge. 2021 continues with Chongqing sitting fifth in the Chinese Super League, with a Champions League Quarter Final to come.

Episodes: 1.1, 2.1, 2.2, 3.1, 3.2, 4.1, 4.2, 5.1, 6.1

Check out the previous episode to see how we have got to in the league, currently sitting in fifth place behind leaders Hebei Huaxia Xingfu.

First, some transfers, as the window had opened for July and I needed a last push for the Champions League final stages.

In came Hong Yujie from Helanshan and Hong Lijun from Beijing to add some quality depth to the squad as the games piled up.


Also drafted in was top top midfielder Chen Yongsen from Shandong for £750k. All needed, as Liao Lísheng had decided he’d had enough and wanted to move on to Shanggang for £1.4M. Good profit on the £500,000 I had spent on him three and a half seasons ago.


I’d not looked too closely at the league results of the other sides in the CSL over the last couple of weeks, as Xingfu were running away with it, and had only dropped a couple of points all season from what I could see. I was a good way behind them in 5th. My priority was player form and of course the Champions League.


Huaxia Xingfu’s results so far this season!

My season was a bit more mixed. Next up was of course, the league leaders, but I am on my own 6 game unbeaten run.


Take that! Tan Long and Mr. Jinx causing all sorts of problems – the game was over after 18 minutes.


The league petered out and I finish 3rd, nowhere near challenging for the title. Not necessary in the Pentagon Challenge luckily, and with Champions League qualification confirmed for next year, I was fully concentrated on this first attempt at silverware.

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Full CSL results

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Pushing forward Tan Long had great effect

The real priorities lay ahead. The Asian Champions League 2nd round.

As in Europe, all of the knockout rounds are two-legged affairs but this competition also includes a home and away final.

I’d drawn Jeju United, winners of the K-League in South Korea in 2020 and winners of their group. Two quick fire goals in the first 14 minutes meant we cruised to a 3-0 win, away from home in the first leg.

Three goals again in the away leg meant a couple of consolations from the Koreans were irrelevant and we progressed!

Next up were the K-League runners up, Ulsan Hyundai. They’d escaped their group which included Shanggang, and beaten CSL title challengers Shenhua 6-4 on aggregate in the 2nd Round.

Again, two quick fire first half goals in the first leg secured the win and took us into the second leg with a solid lead. Tan Junsheng put us ahead, before I sit deep and flooded the midfield to take a 1-1 draw and qualify for the semi-finals!


Of course – who did I draw? My old foes Suwon. If you remember in 6.1, I had faced them in my group already this season, winning once and drawing the other.  The same this time around would be good enough to qualify for my first final.


Tan Junsheng, my trusty attacking midfielder got us ahead in the 10th, before being pegged back in the fourteenth minute. The Suwon centre-back then took an early bath right on half time to give me a perfect chance to take command. Another from Junsheng before a breakaway 3rd in the 84th minute gave me a perfect platform for the home leg in three weeks.

Suwon came to the Chongqing and were suitably dispatched. A nice 17th minute thunderbolt from Mr. Jinx and the tie was over. We are in the final!

Boom! Into my first continental final.  Join me next time to see how we end the season.

Thanks for reading. @AjaxU19s

6.1 – The Turning

Welcome back to my Pentagon Challenge.  Season 6, 2021 and Champions League football comes to the Chongqing Olympic Sports Center.

Episodes: 1.1, 2.1, 2.2, 3.1, 3.2, 4.1, 4.2, 5.1

So on 1st January, in came the three new signings with one foreigner, Emmanuel Gigliotti, leaving us on a free (Episode 5.1). We needed the room and he’d only featured once in the previous season.

With the Champions League campaign starting at the end of February, I only had a few weeks to get the squad fit and back in the loop with my formation.

I’d been training up the boys to play 3 at the back for a full season now, to try to be more solid defensively. Strikerless was clearly working in the league, finishing 2nd. Now I had Chenglong Li (4.1) bombing up the left and new signing Chaker flying down the right wing back slot, I felt I could exploit the crappy CSL full backs as well as those on the continent.

Chongqing v Ulsan_ Chongqing Team Selection Overview

This enabled me to play Tan Long further up the field, with devastating consequences, and my new favourite, 17 year old (Zinedine) Zhu Dan sitting in the middle of the park.

In the ACL I’m drawn against Johor (Malaysian Champions), Osaka AC (Japanese runner up) & Suwon (3rd place in South Korea) in Group H. I’d drawn 0-0 with Suwon in preseason so felt ok about the group with Johor and Osaka not actually having any real players in their squads.

We started with three wins from three in the Champions League, Tan Long picking up 3 goals, with the team scoring 10, including a 4-2 battering of my closest rivals Suwon. A great start.

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The league campaign got off to a flyer too. 6 wins and just two defeats in the opening ten games. A shame that the one defeat was so bad, our players have given the fans their money back! Not seen that before.


A dodgy 3 games in the middle of the season in the league saw 3 loses in a row against mid table sides. The next 11 matches yielded a solid 18 points, taking my tally for the first 21 games to 38 points. 1 point better off than last year but some way off top of the table Huaxia Xingfu.


In the final 3 games in Group H of the Champions League I couldn’t pick up a maximum and only just topped the table.

Asian Champions League_ Overview Stages-1

Drawing Jeju from South Korea in the second round, I felt a bit nervous, as they’d finished second in their group to none other than CSL table toppers Huaxia Xingfu, who’d they’d got two respectable 0-0 draws with. Reading other blogs about the Pentagon Challenge, it sounded like the South Korean teams were the ones to beat, and these guys were the current ACL champions.

Thoroughly dispatched! 6 goals for and two against, this two legged tie only had one winner. 14 minutes into the first leg and we were two up through trusty Alan Kardec and Liào Lìsheng. Three goals in the second leg gave the Koreans too much to do.

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Next up, Ulsan Hyundai, 2020 runners up of the Korean K League, in the quarter finals. Join me next time to see how we get on.

Thanks for reading, and don’t forget to follow me @AjaxU19s on Twitter. Cheers