The first season for an Israeli team to participate in European competitions. Goals by Jerusalem's Avi Cohen (81') and Avi Nimni (87') helped Maccabi Tel Aviv beat FC Volta 2-1 in the first game of the preliminary Champions League, and a 1-0 victory at Ramat Gan Stadium (Meir Melika 23') took the cumulative score to 3-1. The game against Belgian FC Brugge was more challenging and the Yellows were eliminated after losing 1-0 at home and 3-0 away.
Maccabi Tel Aviv was introduced to the UEFA Cup Winners’ Cup (a tournament that was discontinued after the 1998/99 season) with a pair of games against Icelandic Keflavik. Scores of 2-1 in Iceland and 4-1 in Ramat Gan, with goals by Nimni, Klinger, Sevilia and Alon Brumer, were enough to qualify the Yellows convincingly. At the next preliminary stage, Maccabi Tel Aviv was to encounter the strongest European opponent it ever faced, German Werder Bremen. A good first game that ended with no goals was not enough to keep the Yellows in the competition. They lost the next game 2-0 and were eliminated.
Two games against Swiss champion Grasshoppers stood between Maccabi Tel Aviv and a historical debut at the Champions League. The first game in Switzerland ended with a 1-1 tie (Evgeny Kashentsev, 55'), keeping alive the hope for the dream. But the Yellows lost the first European game they hosted at Bloomfield 1-0 and they missed the Group Stage.
Another season in which Maccabi Tel Aviv missed the chance to qualify for the Champions League. Turkish champion Fenerbahce won 1-0 at Ramat Gan Stadium. Throughout most of the return match, the Yellows kept a dramatic 1-1 tie (Eli Drikes, 77'), but they never scored the winning goal to get them to the Group Stage. After the elimination, Maccabi Tel Aviv went on to play against Spanish Tenerife for the UEFA Cup, only to be eliminated from this competition after losing 3-2 in Spain (Ofer Mizrahi 74', Avi Nimni 87') and 1-1 in Ramat Gan (Gadi Brumer 58').
The UEFA Cup’s first preliminary stage gave Maccabi Tel Aviv a home game against Zalgiris Kaunas, which ended in a 3-1 victory with goals by Andjei Kubika (14', 34') and Liron Basis (70'). In the return match, however, the Yellows fell behind 2-0, which spelled elimination, but a dramatic goal by Liron Basis with just three minutes to go pushed them to the next stage. The French team Lens was a much more challenging opponent and Maccabi Tel Aviv was eliminated after a 2-2 tie in the first game (Andjei Kubika 44', Dedi Ben Dayan 85') and a 2-1 loss in France (Liron Basis 24').
Maccabi's greatest victory in Europe was during in the 2001/02 UEFA Cup preliminaries with a score of 6-0 in the first game against Zalgiris Vilna. Dedi Ben Dayan electrified the crowd at Bloomfield in the 7th minute, Dego added a triple (27', 45', 75'), Tal Banin (51') scored his first goal wearing the Maccabi uniform in Europe and Eli Biton (88') secured the final score. At the return game in Lithuania, Rodrigo Goldberg scored (57') for a satisfying 1-0 result, and Nir Levine's players got their ticket to play against Dynamo Zagreb. The first game in Croatia ended in a 2-2 tie with goals scored by Rodrigo Goldberg (23') and Baruch Dego (42'). A 1-1 tie at Bloomfield with a goal by Avi Nimni (41') helped the Yellows move ahead on goal credits. The season's European adventure ended in Holland when Roda beat Maccabi 4-1 (Ferenc Horvath 78'), rendering Eli Biton's pair (38', 58') meaningless at the return match (2-1).
The European season that ended with the national championship is mainly remembered for the fact that UEFA prohibited games on Israeli soil due to the security situation. Despite the restriction, the Yellows did their job against Levadia Tallinn, winning an away game 0-2 with goals by Andrejs Prohorenkovs (4') and Reuven Oved (21'). In the return match in Sofia, Bulgaria, the Yellows won again, celebrating goals by Baruch Dego (74') and Andrejs Prohorenkovs (85'), moving them ahead to play against the Portuguese runner up. The Yellows played their first game against Portuguese Boavista at a stadium in Sofia and won 1-0 with a goal by Baruch Dego (34'). In the return match, the Portuguese managed to overturn the score and win 4-1 (Amir Turjeman 76'), ending Maccabi Tel Aviv's competition in Europe for that year.
This season ended with a European disappointment after Maccabi Tel Aviv was eliminated in the first preliminary round against Slovakian Zilina. The Yellows lost 1-0 in the first game and failed to flip the score during the return match in Italy, ending the game with a 1-1 tie only (John Paintsil).
The only year in which two Israeli groups made it to the Champions League preliminary games. Maccabi Tel Aviv came in second in the Israeli league but still made it to Europe. The race to the Champions League began with games against HIK Helsinki of Finland, which ended 0-0 away and 1-0 in Bloomfield, with a goal by Liran Cohen three minutes before going into overtime. The next stop was Thessaloniki against the local PAOK, which Maccabi Tel Aviv won 2-1, with goals by Ishmael Addo (13') and Erez Mesika (43'). It later became known that the Greek team included a player against regulations, and Maccabi Tel Aviv was granted a technical victory of 3-0. The Yellows left no room for doubt and won the return match 1-0 (Liran Cohen 8'). For the first time in the Club’s history, they went on to the Group Stage of the Champions League.
In the UEFA Cup preliminaries, Maccabi Tel Aviv met a rival from nearby, Apoel Nicosia of Cyprus. The game was harder than expected, and the Yellows lost 1-0 in Cyprus. At the return match at Bloomfield, goals by Avi Nimni and Erez Mesika made for a 2-2 tie score that ended Maccabi Tel Aviv’s European dream.
The European chapter of the UEFA Cup preliminaries began with one of the worst defeats in the European competition. Maccabi Tel Aviv suffered a 1-0 loss in Andorra against the amateur Santa Coloma. The Yellows overcame the shame and won over the Andorrans 4-0 at Bloomfield with a pair by Yannick Kamanan (12', 71') and additional goals by Erez Mesika (25') and Yossi Shivhon (63'). At the next stage, Maccabi Tel Aviv surrendered to Turkish Archespore, ending with a home game tie 1-1 in its first game (Yannick Kamanan 60') and losing 3-1 at the return match (Rudy Haddad 41').
After a three-year absence from Europe, the Yellows returned for three rounds in the European league preliminaries. In the first round of games, the team played against Montenegran Mogren, winning 2-0 at Bloomfield (Yoav Ziv 49', Harris Medunjanin 52') and losing 1-2 in the return match (Harris Medunjanin 7'). In the next round, Maccabi Tel Aviv faced a very strong rival, the Greek Olympiakos. The game was played without fans following to a UEFA penalty, but the Yellows scored a goal (Harris Medunjanin 18') in their 2-1 away loss. In the return match, Maccabi Tel Aviv knew that a 1-0 victory would suffice for a ticket to the next round, and Roberto Collauti (42') realized the dream with a goal near halftime. In the playoffs for the ticket to the Group Stage, Avi Nimni's players met the daunting Paris St. Germain. The French won 2-0 in Paris. Both teams put on a wonderful display at the return match at Bloomfield, ending with St. Germain’s disappointing 4-3 loss to Maccabi Tel Aviv with by a pair scored by Eliran Atar (48', 95') and goals by Yuval Avidor (68') and Harris Medunjanin (83').
As in the previous season, Maccabi Tel Aviv met three rivals at the Europa League preliminaries, and this time the ending was better. In its first round, Maccabi Tel Aviv hosted Khazar Lankaran of Azerbaijan and won 3-1 (Moussa Konate 22', Eliran Atar 39', Guillermo Israelevich 44'). After a no-goal tie at the return match, the Yellows met the Bosnian Zeleznicar and won 2-0 at the away game (Roberto Collauti 47', 56'). In the return match, Moti Iwanir's players exploded with a 6-0 score to equal the team's prior record win in Europe. This victory saw a pair by Collauti (18', 45'), another by Eliran Atar (54', 86'), a wonderful free kick Rafi Dahan (38'), and an own goal by defender Vasilyevich (81'). The drawing in Switzerland called for Maccabi Tel Aviv and Panathinaikos to duel over the ticket to the Europa League Group Stage. After a 0-0 halftime score at Bloomfield, Moussa Konate (60') and Eliran Atar (67', 90') scored three times. Harris Medunjanin (61') scored at the return match in Athens and even two goals by the Greek team were not enough to beat Maccabi. The team made history with its first appearance at the Europa League Group Stage.