The first season an Israeli team participated in European competition. Goals by Avi Cohen (81') and Avi Nimni (87') helped Maccabi Tel Aviv beat Maltese side FC Valetta 1-2 in the away leg of the Champions League first round qualifiers, and a 1-0 victory at Ramat Gan Stadium (Meir Melika, 23') handed Maccabi a 3-1 aggregate victory. The contest against Belgian side FC Brugge in the second round was more challenging and Maccabi were relegated from the competition after losing 0-1 at home and 3-0 away.
Two legs against Swiss champions Grasshopper were all that stood between Maccabi Tel Aviv and an historic debut in the group stages of the Champions League. The first game in Switzerland ended in a 1-1 draw (Evgeny Kashentsev, 55'), keeping the historic dream alive. But Maccabi lost their first ever European game hosted at Bloomfield Stadium 0-1 and were forced to wait for a future opportunity.
Another season in which Maccabi Tel Aviv missed the chance to qualify for the Champions League. Turkish champion Fenerbahce won 0-1 at Ramat Gan Stadium. Throughout most of the return match, Maccabi dramatically stayed level at 1-1 (Eli Driks, 77'), but they failed to find the winner that would get them to the Group Stage. After being eliminated, Maccabi went on to play Spanish side Tenerife in the UEFA Cup qualifiers, only to be religated from this competition after losing 3-2 in Spain (Ofer Mizrahi 74', Avi Nimni 87') and 1-1 in Ramat Gan (Gadi Brumer 58').
This season's European campaign ended in disappointment after Maccabi Tel Aviv were eliminated in the first qualifying round by Slovakian side MSK Zilina. Maccabi lost 1-0 in Slovakia and failed to overturn the tie at the return match played in Italy, which ended in a 1-1 draw (John Paintsil, 25').
The only year in which two Israeli teams made it to the Champions League qualifying rounds. Maccabi Tel Aviv finished the 2003/04 Premier League season in the second spot but still qualified for Europe's pre-eminent competition. Qulaification for the Champions League group stage began with games against HJK Helsinki of Finland, which ended 0-0 away and 1-0 at Bloomfield, with a goal by Liran Cohen three minutes before injury time. The next stop was Thessaloniki in Greece to face stalwarts PAOK , a game which Maccabi won 1-2, with goals by Ishmael Addo (13') and Erez Mesika (43'). It later emerged that the Greek team had fielded an ineligible player and Maccabi were granted a technical 0-3 victory. Despite the already formidable aggregate lead, Maccabi left no room for further doubt when they also won the return match 1-0 (Liran Cohen 8'). For the first time in the club’s history, Maccabi Tel Aviv had qualified for the group stage of the Champions League.
Maccabi's European campaign started mid-July with the second qualifying round of the Champions League. The team succeeded in starting that campaign on the right foot with victories in both legs against Hungarian champions Gyori, 0-2 away and 2-1 at home at Bloomfield Stadium.
The next hurdle, the third qualifying round, proved to be far higher as Maccabi drew the toughest possible opponent, Swiss champions FC Basel. After losing by the smallest of margins, 1-0, in the away leg, Maccabi were already trailing 0-3 after half an hour in the return leg at Bloomfield Stadium. A Basel own goal, and a second by midfielder Eran Zahavi, returned hope to the hearts of the Maccabi faithful even before the referee's halftime whistle. In the second half Maccabi continued their momentum and midfielder Mahran Radi equalised just after the restart. But the home side failed to find the two additional goals that would have given them the winning aggregate and at 3-3 Maccabi made their exit from the 2013/14 Champions League competition.
Maccabi were then destined to compete in the final play-off round of the Europa League against Greek side PAOK Thessaloniki, but the suspension of Ukrainian side FC Metalist Kharkiv, who defeated PAOK in the Champions League qualifiers, returned the Greeks to the premier European tournament and handed Maccabi Tel Aviv a free pass to the Europa League group stage.
After a second consecutive Israeli Premier League championship, Maccabi Tel Aviv opened yet another chapter in their European history in the second qualifying round of the Champions League with a second all-time encounter with Andorran champions Santa Coloma. Owing to the ongoing conflict at the time on Israel's southern border, Maccabi Tel Aviv were forced to play all of their home matches in Larnaca in nearby Cyprus, at the Antonis Papadopoulos Stadium of first division side Anorthosis Famagusta FC. The first leg against Santa Coloma was played in Andorra and a second-half Rade Prica strike gave Maccabi a valuable away goal in a 0-1 win. In the return leg, Eran Zahavi scored from the spot and Tal Ben Chaim added on to complete a 3-0 aggregate win and advance Maccabi into the third qualifying round.
In the third round Maccabi drew Slovenian champions NK Maribor and in the first leg played at their Ljudski Vrt Stadium, home-side midfielder Damjan Bohar scored a dramatic injury-time winner to give his side a 1-0 victory. In the return leg, played once again in Cyprus, Maccabi managed to turn around a one-goal deficit to take a 2-1 lead early in the second half courtesy of goals on either side of the break by Tal Ben Chaim and Eden Ben Basat. A third Maccabi goal would have sent them into the Champions League play-offs at the expense of their rivals, but just moments later an Agim Ibrahimi equaliser put an end to the Maccabi dream. The 3-2 aggregate in Maribor's favour meant Maccabi Tel Aviv would continue their European campaign in the play-off round of the Europa League.