Zola's transformation from midfield magician to coach has been a tough one and on Sunday his relegation-threatened West Ham host Premier League leaders Chelsea in front of an Upton Park crowd rapidly losing confidence in his managerial ability.
A 3-1 defeat by Bolton Wanderers on Tuesday left West Ham in dire straights and the looming Christmas fixtures are hardly a source of festive cheer, starting with the ultimate test against Chelsea who got back to winning ways on Wednesday after a blip.
The fixture pits Zola against Carlo Ancelotti, the man responsible for him joining Chelsea after he decided that he had no further use for him at Parma in 1996.
Ancelotti's Chelsea scraped a 2-1 victory over Portsmouth which hoisted them three points above Manchester United at the top of the table. West Ham, meanwhile, are languishing second from bottom with just three league wins from 17 matches.
Zola's assistant Steve Clarke, who moved across London after many years as number two at Chelsea, most notably during the Jose Mourinho era, has tried to take the pressure off Zola's shoulders, saying the club's poor form was his responsibility.
Zola also appears to have plenty of support from his old team mates at Stamford Bridge, although he can expect no early Christmas presents on Sunday.
"I have a lot of respect for Gianfranco and Clarkey and I don't want to see them do badly at all," Frank Lampard, who joined Chelsea from West Ham in 2001, said after his late penalty earned victory against Portsmouth.
"They're great lads. It's difficult but then it's a difficult league."
Zola, who replaced Alan Curbishley last year, has not been helped by injuries to key players such as striker Carlton Cole, while the club's financial situation has added to the gloom.
Clarke, however, believes the visit of his old club can give the Hammers a lift. "It's a great game for us," he told the club's website. "Nobody expects us to get anything but in football you never know."
With Chelsea not playing until Sunday, champions Manchester United can again draw level on 40 points although Alex Ferguson's side face a tricky away fixture to Fulham where they were beaten 2-0 last season.
Fulham, who reached the knockout phase of the Europa League on Wednesday, are strong at home and United will be guaranteed a tougher examination than the one they had in midweek when Wolverhampton Wanderers fielded a second-string side, gifting United a 3-0 win at Old Trafford.
Third-placed Arsenal, eight points behind Chelsea with a game in hand, face Hull City at the Emirates on Saturday while in-form Aston Villa host Stoke City.
Fifth-placed Tottenham Hotspur, who inflicted a 3-0 defeat on Manchester City on Wednesday, are at Blackburn Rovers.
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