Long-time team-mates through the academy ranks, the pair have become perennial loanees, both taking in their first spells away from Liverpool in 2015.
Ojo joined Wigan in the Championship, while Wilson was given a taste of League One football with nearby club Crewe Alexandra.
Both took up regular roles with the Bluebirds, with Ojo scoring five goals and assisting seven in 42 games while Wilson netted seven and teed up 12 in 39 outings.
Cardiff manager Mick McCarthy expressed a desire to keep the pair in south Wales, insisting Liverpool would need to “sort themselves out” when it comes to his two targets.
But as they gear up for the new campaign, Ojo and Wilson find themselves in starkly different positions when it comes to their future.
Part of the Wales squad at the Euros, Wilson will report back for pre-season training later this month amid speculation over a move to Benfica, Brentford or West Brom, with a £12.8 million price tag over his head.
Instead, the 24-year-old was told to return to Kirkby, where he has joined Barry Lewtas’ under-23s squad for training sessions and friendlies.
He isn’t the first and he won’t be the last to be omitted from the senior squad – there is an obvious logistical explanation, with a 34-man squad in Salzburg to be increased by 10 more in the coming weeks – but it is a frustrating situation nonetheless.
It is a particularly strange situation, too, when considering the fact that only seven academy graduates have made more appearances for the first team during Klopp’s near six-year reign than Ojo’s 13.
That is more than contemporaries such as Woodburn, Ryan Kent, Jordan Rossiter, Jerome Sinclair, Pedro Chirivella, Ovie Ejaria, Cameron Brannagan, Joao Carlos Teixeira, Connor Randall, Sergi Canos, Joe Maguire and, of course, Wilson himself.
Back in 2011, Liverpool believed they had pulled off a coup in convincing a 14-year-old Ojo to join from MK Dons, spurning advances from the biggest clubs across the Premier League and the rest of Europe.
Ojo has claimed that Chelsea, Man United, Man City, Everton, Tottenham, Fulham and his boyhood club Arsenal were interested from England, while Barcelona, Real Madrid, Ajax, Inter Milan and Juventus made advances from abroad.
Unsurprisingly, the winger was reluctant to swap England for Spain, Italy or the Netherlands at such a young age, and opted for Liverpool due to a clearer pathway to the first team.
The Reds parted ways with a then-record fee for a 14-year-old, paying a reported £2 million to the League One club.
Given Ojo made his Liverpool debut as an 18-year-old, in the 2-2 draw with Exeter City in the FA Cup third round at the start of 2016, he will have felt vindicated for choosing the Reds over the array of elite clubs also chasing his signature.
But somewhere between the 11 appearances, four assists and one goal in Klopp’s first season and now, things have gone sour.
There were injury problems and questionable career decisions – an ambitious move to Stade de Reims in Ligue 1 for 2018/19 chief among those – but there was also a lot of mystery behind his fade out of the picture.
His last involvement at first-team level was during pre-season in 2018, when he played six times, scoring twice and assisting twice, including a penalty against Man United in Michigan.
That 4-1 victory over United saw him share the pitch with Curtis Jones, Nat Phillips and Caoimhin Kelleher, but while they have established themselves on the senior stage in the years since, Ojo has drifted into obscurity.
It is a sad, quiet decline for a player once deemed worthy of a seven-figure outlay at just 14, and it poses the question: what next?
While there is strong interest in Wilson both at home and abroad, with Liverpool expecting to seal a lofty fee for the playmaker, there is no indication of an imminent move for Ojo.
No price tag mooted, no clubs reported to be in pursuit, no mileage on the rumour mill.
Buried at Kirkby, filling in for the likes of Mateusz Musialowski, Kaide Gordon and Harvey Elliott – players at least six years his junior but part of Klopp’s squad in Austria – Ojo has been almost forgotten.
Liverpool remain in a strong position when it comes to both Ojo and Wilson, as though they have entered the final year of their contracts, the club hold the option of extending those by a further 12 months.
In order to capitalise on their value, they will almost certainly do so, which puts their No. 54 in a difficult position if he is to seek a permanent exit.
There is a body of work to suggest he is worth a punt, with Ojo having now clocked 91 appearances in the Championship, 19 in the Scottish Premiership, 15 in Ligue 1 and eight in the Premier League.
His most productive spells have come with Rangers and Cardiff, which suggests he could settle and, hopefully, thrive in either the English second tier or the top flight north of the border.
It is the move Ojo needs at this stage in his career, as it has been made patently clear that he is now surplus to requirements for the club who shelled out a record fee for his services a decade ago.