Rangers must now hope they can overturn a single goal deficit when the sides clash again in a fortnight’s time, something they were unable to do in their Champions League qualifier with CSKA Moscow, and this time without an away goal in the bank.
A place in the first ever group stage of the UEFA Cup is certainly not beyond McLeish’s men but this Portuguese side will be no pushovers at Ibrox, especially against a Rangers side that will be forced to play largely on the attack.
Dark clouds had gathered ominously over the picture postcard setting of Funchal bay ahead of kick-off as Rangers looked to break a winless streak in Europe that had stretched to seven games.
On a humid night the pace of the match was surprisingly quick, with the home side in particular bursting forward with alacrity and purpose in regular bursts.
Rangers’ failure to convert chances into goals has been their downfall in domestic competition this season and it was a similar tale as darkness descended in Madeira.
Shota Arveladze’s inclusion in the side – at the expense of Paolo Vanoli – saw Dado Prso switch to a left-wing role with Arveladze partnering Nacho Novo in attack.
The Spaniard had Rangers’ best chances of the match, stabbing a volley onto the post from around six feet and then fastening on to Prso’s knockdown only to see Marcos deny him with an athletic block from a matter of yards.
Chris Burke was again asked to supply the ammunition at set plays and from one such free kick Prso headed narrowly wide before nodding a swirling Burke corner against the outside of the post.
Even without strikers Krum Bibishkov and Pena – ineligible for this tie – and the injured Silas, Maritimo still looked a potent force up front.
A 4-5-1 formation quickly became 4-3-3 as Alan and Luis Felipe hared down the flanks at great speed to support Manduca up front.
They seemed able to dissect the Rangers midfield almost at will and playmaker Leo Lima set the tone for the evening as early as the fifth minute with a fierce drive that slid only inches past Stefan Klos’ right-hand post.
Klos was to become one of the key protagonists as play unfolded with the keeper clutching a shot from Alan before tipping over another powerful effort from the lively Lima.
The keeper was helpless, however, when faced with Felipe on 23 minutes after the midfielder had skipped past Craig Moore only to slide his shot erroneously wide.
Maritimo were not so slack two minutes later when they grabbed the goal their prodigious work ethic had deserved.
Lima was the man at the centre of it again. The Brazilian hammered another ferocious attempt on goal, Klos parried only for Manduca to gleefully ram the loose ball home.
The incessant parping of trumpets and banging of drums from the local brass band in one corner of the stadium had turned this into one part football match, one part Notting Hill carnival but Rangers certainly weren’t enjoying the festivities at this stage.
Alan had a chance shortly before the break to extend Maritimo’s lead but Klos smothered the attempt before Arveladze headed another pinpoint Burke delivery high over the crossbar.
Maritimo entered this clash boasting the proud record of only one European defeat at home – to Italian heavyweights Juventus – and Rangers rarely looked like they would be adding their name to that short but exclusive list after the break.
A Fernando Ricksen deflected free kick that sailed into the midriff of Marcos offered some light but play was soon raging around Klos’ goal again as a Ferreira cross almost presented Tonel with a golden chance before the ball was eventually cleared.
In the heart of the midfield, Lima was entertaining the boisterous local crowd with a nice line in showboating – at one point cheekily trying to chip Klos from the halfway line – before Manduca threatened again with a sharp drive that arced narrowly wide.
Rangers rallied and the unfortunate Novo saw another goalbound attempt blocked by the elastic Marcos in the home goal as the Light Blues tried to counter the steady stream of Maritimo attacks.
The pace of the game gradually dropped as the sapping heat took its toll on the players, with substitute Joel bringing another spectacular stop out of Klos.
Rangers were unable to find a way past Marcos with some late half chances but if they are to stay in Europe beyond September they must find a way to do so in a fortnight.
Failure to do so will mean a European campaign as short as the infamous runway at Madeira airport.
RANGERS (4-4-2): 1 Klos; 21 Ross, 4 Boumsong, 3 Moore, 24 Vignal (Vanoli 56); 17 Burke, 2 Ricksen, 14 Mladenovic, 9 Prso; 7 Arveladze, 10 Novo (Lovenkrands 82)
Subs not used: Smith, Malcolm, Khizanishvili, Hughes, Thompson
Booked: Ricksen (42)
MARITIMO (4-5-1): 26 Marcos; 2 Ferreira, 25 van der Gaag, 4 Tonel, 21 Briguel; 20 Filipe (Joel 55), 10 Lima (Zeca 84), 15 Wenio, 23 Chainho, 11 Alan; 22 Manduca (Zumbi 72)
Subs not used: Nelson, Bino, Souza, Fernando
Booked: None
Rangers’ Man of the Match: Stefan Klos