Gallagher spent last season on loan at Crystal Palace, where he impressed with a string of fine performances, resulting in a call-up to the England squad.
His stint at Selhurst Park was reminiscent of Lingard's successful loan spell at West Ham in 2021, but, whilst it appeared that Lingard was getting his career back on track, his subsequent return to Old Trafford provided more misery.
The 29-year-old fell down the pecking order and ultimately left the club after 11 years this summer as a free agent, with his career again at a crossroads.
Darren Ambrose believes Lingard's unsuccessful Old Trafford return should be a warning to Gallagher when choosing where to play his club football this season.
The 22-year-old starlet could choose to fight for a place at Stamford Bridge, but Everton and Aston Villa are reportedly keen on taking him on a short-term deal, while a return to Palace could also be an option.
And ex-Eagles star Ambrose says another season on loan wouldn't hamper his England chances.
"I keep going back to the Jesse Lingard situation - learn from his mistakes because I think it was a mistake going back to Manchester United," Ambrose told talkSPORT.
"Gallagher has to go somewhere he is going to play. If Thomas Tuchel has promised him games and he can play and is confident enough to stay at a huge club like Chelsea, go for it.
"There's an opportunity that if he stays at Chelsea and plays half the games, he could still play for England.
"But if he goes to Everton or Palace and plays all the games, it's not really about the club any more.
"If you're playing every game at the top four, you're more than likely to be picked for England in my opinion, but if you look at the players Southgate picks, Marc Guehi and Tyrick Mitchell have been selected before."
Chelsea are reportedly open to sending Gallagher out on loan again this season, with plenty of interest after his dazzling campaign, as he was named Crystal Palace's Player of the Year.
But with a taste of international football now under his belt and the World Cup approaching, Gallagher may opt to stay at Chelsea if he believes playing for a title contender will enhance his chances of booking his ticket to the Qatar 2022 World Cup.
Gallagher turned heads last season, scoring eight times and providing three assists in 34 Premier League appearances for Patrick Vieira's side, helping the Eagles to a mid-table league finish and the FA semi-final.
The talented midfielder will not be short of suitors this summer if Chelsea do decide to send him on a fourth-consecutive season-long loan, but his choice of club could be instrumental in whether or not he secures a seat on the plane to Qatar.