The Portuguese was a key component in Ange Postecoglou's treble-winning Celtic machine, hitting double figures in both goals and assists in the 2022-23 Scottish Premiership season with 11 of his own and 10 assists.
As Postecoglou made the move to North London, Jota also headed for the Celtic Park exit door, joining the Saudi Pro League revolution in a £25.2m switch to reigning champions Al-Ittihad.
Jota featured regularly in his earliest days with Nuno Espirito Santo's side, scoring his first goal on his fourth appearance against Al-Wehda in August, but the 24-year-old has since been consigned to the fringes.
Al-Ittihad also brought Karim Benzema, N'Golo Kante, Fabinho and Luiz Felipe to the club from Europe in the summer, which saw the champions go over their permitted quota of eight foreign players, meaning Jota was left out of their domestic squad.
The former Celtic man is still able to compete for Al-Ittihad continentally and started an AFC Champions League win over Al-Quwa Al-Jawiya last month, but he has sat out each of his side's last six Saudi Pro League fixtures.
Santo's decision to axe Jota from the ranks has inevitably led to speculation surrounding the winger's long-term future, and it has even been claimed that he could terminate his Al-Ittihad contract, which runs until 2026.
Amid the uncertainty, a reunion with Postecoglou at Tottenham has been mooted, and Football Insider claims that the Premier League leaders are keeping a close eye on how the situation develops.
While Postecoglou would welcome the chance to work with Jota again, the report adds that Spurs would only be open to a loan deal midway through the campaign, given his £200,000-a-week wages and lack of domestic football.
The Lilywhites have not been short of attacking firepower this term, with James Maddison and Son Heung-min already collecting Premier League Player of the Month awards for their contributions this term.
Maddison's fellow new signing Brennan Johnson is also at Postecoglou's disposal, as are Bryan Gil, Alejo Veliz, Richarlison and Dejan Kulusevski, whose move from Juventus was made permanent over the summer.
However, no fewer than three left-sided options are currently sidelined with serious injuries, as Manor Solomon and Ivan Perisic are both on the long road to recovery from knee operations.
While Solomon could target a return in January, there are fears that Perisic - whose ACL problem is far more severe - could have played his last game in a Spurs jersey ahead of the expiry of his contract in 2024.
Meanwhile, the luckless Sessegnon has not played a competitive match yet this season due to a recent thigh operation, and it is unclear when the Englishman might be considered for selection again.
Despite their fitness woes, Spurs sit at the top of the table with 26 points from their opening 10 games - a tally that no manager had ever achieved before in the Premier League - and they have until Monday to prepare for a tantalising London derby with Chelsea.