Rangers' fortunes have taken a remarkable dip in the past 12 months and now their Champions' League campaign is over in the qualifying stages. Fenerbahce scraped to a 2-1 win in the Sukru Saracoglu stadium to secure a place in the group stage estimated to be worth about £10m.
Rangers could legitimately have argued they had been the better team. But an early goal from Haim Revivo and a second from his replacement Serhat Akin after 70 minutes were the most significant statistics on the night. Fernando Ricksen's deflected reply turned out to be nothing more than a consolation. The Glasgow team must now try their luck in the Uefa Cup alongside Kilmarnock and Hibernian.
This represents another major setback for manager Dick Advocaat, who, until Martin O'Neill arrived at Celtic, could do no wrong in Glasgow. Many words had been spoken before the match and among the wisest came from the Rangers midfielder Claudio Reyna. The American, who was not to last the first half due to a groin injury that flared up, had warned of the need to avoid conceding free-kicks in dangerous positions.
Yet four minutes were not yet on the clock before Scott Wilson had upended Samuel Johnson just outside the area. The defender looked aghast at Pierluigi Collina's decision but for Haim Revivo it was just perfect. Stefan Klos helped him by deciding to remain off his line as he marshalled his wall. The Israeli could see the part of the goal he wanted to hit and an outstretched Klos could not keep the shot out.
Maurice Ross was given his first taste of Champions' League action when he replaced Tony Vidmar at the break as Rangers switched from four at the back to three central defenders. Ross almost made an instant impact, winning a corner, then popping up at the far post to set up Wilson, who was crowded out.
Fener were hardly creating anything themselves and needed goalkeeper Rustu Recber to save them when the forward Andrei Kanchelskis played Ricksen in behind Abdullah Ercan to blast a drive that the goalkeeper tipped over. However, the home fans saw Akin on for Revivo in the 70th minute and the newcomer's first touch beat Klos into the net.
Rangers threw Claudio Caniggia on in place of Kanchelskis and within two minutes Ricksen had pulled a goal back courtesy of a hefty deflection. The final few minutes saw Rangers throwing bodies forward but the home side held on.
Fenerbahce: Recber, Meric, Temizkanoglu, Dogan, Mirkovic, Rapajic (Andersson, 77), Revivo (Akin, 70), Ozat, Lazetic, Ercan, Johnson. Substitutes not used: Akdeniz, Simsek, Gunes, Denizhan, Daglaroglu.
Rangers: Klos, Wilson, Amoruso, Vidmar (Ross, h-t), Numan, Ricksen, Konterman, De Boer, Kanchelskis (Caniggia, 80), Reyna (Hughes, 37), Flo. Substitutes not used: Christiansen, Dodds, Latapy, Miller.
Referee: P Collina (Italy).