Chelsea play last year’s Semi-Finalists Ajax tomorrow night in the heavyweight battle of Group H. The two clubs that will grace the Johan Cruyff Arena share no fewer than five European Cups between them. Both will field exciting young playing XIs that hope to dazzle Europe like in days gone by.

This piece will explore the four players that have plied their trade at both SW6 and Amsterdam over the years. Interestingly, I feel a distinct sense of ‘what could have been?’ as I read off the names; with each perhaps failing to fulfil their full potential at Stamford Bridge.

Jesper Gronkjaer

Gronkjaer is now a pundit in his native Denmark
(Photo by Clive Brunskill/Getty Images)

Where would our club be without this man? 

Jesper Gronkjaer will forever be in the hearts of every Chelsea fan for scoring that goal against Liverpool in 2003 to secure the bankrolling of Mr Abramovich. The crafty winger moved to Chelsea in 2000 for £7.8m after an illustrious career at Ajax. Gronkjaer lifted a Dutch Cup with Ajax in 1999, scoring a mesmerising brace at in the final at De Kuip.

I feel a distinct sense of irony when I write that he failed to win a single major at Stamford Bridge; leaving for Birmingham almost immediately after laying down the foundations for our glorious takeover. 

Thank you, Jesper!

Bertrand Traore

Bertrand Traore is now playing for Lyon in Ligue 1

Another player to leave Chelsea empty-handed, there can be no denying the talent of 24 year old Bertrand Traore. After rejecting Manchester United for the famous Chelsea Academy, Traore played sixteen games for the First Team during our catastrophic 2015-16 campaign.

Always a handful in the box, many Chelsea fans believed the club made a mistake loaning him to Ajax in 2016, scoring thirteen goals to help them to the Europa League Final.

This impressive campaign in the Netherlands led to interest from Lyon, buying him from the Blues on his return in 2017.

However, this may not spell the end for Traore at Chelsea. The club inserted a “buy-back clause” during his sale. With buyback clauses being barred in French football, it’s more of a gentleman’s agreement with Lyon, and there may be a distinct possibility if his rich goalscoring form in France continues.

Filipe Luis

Filipe Luis won a League Cup and Premier League Title in his year at Stamford Bridge.

Ok, I’ll admit it. This is a longshot. 

Filipe Luis was eighteen when he was signed for Ajax from Brazil in 2004, never being capped by the club. It would be fair to say he experienced his first taste of football in Europe warming the bench in Amsterdam.

Four clubs later, Chelsea purchased a more mature Filipe Luis for £16m in 2014 as reliable left-back cover for Cesar Azpilicueta.

Never truly given the chance under Jose Mourinho, he left after in 2015 after a solitary title-winning season at Stamford Bridge.

Our defensive struggles the season after seem to tell us this was a mistake.

Winston Bogarde

Bogarde earned over £15m during his four year stint at Stamford Bridge.

Oh dear.

Winston Bogarde was a fantastic player, winning the Champions League with Ajax in 1995.

He later became a defensive stalwart at Barcelona, a key part of the side that won a historic treble in 1997-1998.

The man seemed a born winner, and in 2000 looked the perfect big-name candidate to stabilise our defence and spearhead the next stage of the Blue Revolution that had been started by Vialli, Zola and Co.

If only.

Bogarde signed a four-year contract for Chelsea, earning over £40,000 per week.

No problem. Except, we weren’t that rich back then. And, no, he wasn’t the first name on the teamsheet. After Gianluca Vialli was replaced by Claudio Ranieri September 2000, he was immediately discarded and asked to leave.

But, no. Money ranked significantly higher than first team football for Bogarde, and he remained at the club for a further four years.

He played nine times.

All while pocketing £40,000 every single week.