Fielding a weakened team after six of their players preferred to stay at home because of the worsening security situation in the region, Chelsea weathered the pressure and even survived the 53rd minute sending off of Mario Melchiot for kicking out at home skipper Shimon Gershon.
However, they couldn’t hang on and conceded two late goals as the Israeli team gained a vital advantage ahead of the second leg.
Gershon opened the scoring in the 86th minute from the penalty spot after a handball from John Terry before Serguei Klashenko headed the second in the last minute past Mark Bosnich who was making his long-awaited debut.
Chelsea had travelled to Israel without skipper Marcel Desailly, Emmanuel Petit, Eidur Gudjohnsen, Graeme Le Saux, William Gallas and Albert Ferrer who all refused to make the trip fearing for their safety in the region.
Leeds beat French club Troyes 4-2 at Elland Road. A pair of goals each from Australia striker Mark Viduka and midfielder Lee Bowyer ensured victory for the English Premiership side.
But Patrice Loko gave Troyes hope for the second leg with two away goals. Troyes suffered a late blow when Algeria international Medhi Meniri was sent off for elbowing Viduka.
Troyes coach Alain Perrin said he feared Leeds could pile on the misery for his men in the return match.
Glasgow Rangers gave themselves a great chance of reaching the next round with a 3-1 win against Dynamo Moscow.
Lorenzo Amoruso opened the scoring after nine minutes with Michael Ball adding the second on 61 minutes. Ronald De Boer scored on 80 minutes but Rolen Gusev scored in the last minute to give the Russians some hope.
It was a good night for the Italian clubs with victories for AC Milan, Inter Milan, Parma and Fiorentina.
Manuel Rui Costa (20 minutes) and Andrey Shevchenko (50) gave AC Milan a 2-0 win at home against CSKA Sofia of Bulgaria.
Portuguese midfielder Rui Costa fired inside Nenad Lukic’s near post from 20 yards to give the hosts the lead before Shevchenko, set up by a run and cross by Brazilian substitute Serginho, made it 2-0.
City rivals Inter, bidding to win the UEFA Cup for a fourth time, defeated Wisla Krakow with both goals coming from Sierra Leonian striker Mohamed Kallon.
His first goal came when he headed in from close range after a shot by Brazilian Adriano had rebounded off the bar while the second was an acrobatic volley.
Fiorentina saw off FC Tyrol 2-0 with goals from substitute Domenico Morfeo and Nuno Gomes. The win was revenge for Fiorentina who lost 5-3 to the Austrians in the same competition last season.
Parma won 3-1 at Utrecht with two goals from Marco Di Vaio and one from Emiliano Bonazzoli.
Last year’s Champions League runners-up Valencia were indebted to Romanian international Andrew Ilie for giving them a vital away goal in a 1-1 draw against Legia Warsaw in Poland.
Ilie stroked home a 61st minute penalty following a foul on striker John Carew. The Spaniards had fallen behind to a goal from Bartosz Karwan after just 12 minutes.
Collated results on Thursday:
In Vigo:
Celta Vigo 3 Slovan Liberec 1
In Utrecht:
Utrecht 1 Parma 3
In Zaragoza:
Real Zaragoza 0 Servette 0
In Trieste:
Inter Milan 2 Wisla Krakow 0
In Ipswich:
Ipswich Town 0 Helsingborg 0
In Glasgow:
Rangers 3 Dynamo Moscow 1
In Leeds:
Leeds United 4 Troyes 2
In Paris:
Paris St Germain 4 Rapid Vienna 0
In Varazdin:
Varteks Varazdin 3 Brondby 1
In Florence:
Fiorentina 2 Tirol Innsbruck 0
In Milan:
AC Milan 2 CSKA Sofia 0
In Berlin:
SC Freiburg 0 St Gallen 1
In Tel Aviv:
Hapoel Tel Aviv 2 Chelsea 0
In Halmstad:
Halmstad 0 Sporting Lisbon 1
In Thessaloniki:
PAOK Salonika 6 Pribram 1
In Zurich:
Grasshoppers 4 Twente Enschede 1
In Bordeaux:
Girondins Bordeaux 2 Standard Liege 0
In Warsaw:
Legia Warsaw 1 Valencia 1
In Copenhagen:
FC Copenhagen 0 Ajax Amsterdam 0
In Osijek:
Osijek 1 AEK Athens 2
In Berlin:
Union Berlin 0 Litex Lovech 2
In Kiev:
CSKA Kiev 0 Club Bruges 2
Played on Tuesday:
In Kerkrade:
Roda JC Kerkrade 4 Maccabi Tel Aviv 1
In Stavanger:
Viking Stavanger 0 Hertha Berlin 1
—AFP/Reuters