But Sporting goalkeeper Rui Patricio succeeded only in colliding with his own player and received a bloody nose for his troubles.
After two minutes of treatment, the 20-year-old Patricio found himself in deeper trouble when McCann's long punt was chased by Helguson.
Patricio came racing out of his area and not only looked to have handled the ball well outside his area - but also caught Helguson late with an ill-judged challenge which left the Iceland striker poleaxed on the ground.
Helguson rose gingerly to his feet but there was no punishment for Patricio.
Soon after Bolton opened the scoring with a goal that so typifies the footballing philosophy which harvested so much success under former boss Sam Allardyce.
Hunt's long pass forward to the ever-willing Kevin Davies, was flicked on dangerously just inside the 18-yard box.
Helguson touched the ball on to Taylor and although his shot was blocked, McCann strode forward to sidefoot the ball home right-footed from 14 yards.
Six minutes before the break it was almost 2-0 but Taylor's right-foot shot from 20 yards flew inches wide of Patricio's left-hand post.
Heidar Helguson was unlucky to see his second-half header hit the bar
And Bolton were unlucky not to double their lead in the 53rd minute.
Sporting failed to deal with a long cross from Ivan Campo as Davies flicked the ball on at the near post.
Helguson was arriving just behind him to head goalwards only for the ball to rebound off the crossbar and to safety.
But there was a growing sense of unease among the home supporters as their side failed to convert their dominance into goals, particularly when Leandro Romagnoli hit the bar with a brilliant diagonal shot.
Those Bolton fans' fears proved well-founded in the 68th minute when Vukcevic produced a devastating finish to draw Sporting level.
Bolton defender Gary Cahill allowed Rodrigo Tiui to head Miguel Veloso's long punt forward and Vukcevic cracked an unstoppable left-foot volley past Ali Habsi from 18 yards.
Both sides had chances late on through Vukcevic and Taylor but Sporting left with the advantage ahead of the second leg in Lisbon.
Bolton: Al Habsi, Hunt, Andrew O'Brien, Cahill, Gardner, Campo (Teymourian 84), Davies, Joey O'Brien (Guthrie 67), McCann, Taylor, Helguson (Giannakopoulos 55). Subs Not Used: Walker, Samuel, Meite, Vaz Te.
Booked: Joey O'Brien, McCann.
Goals: McCann 25.
Sporting: Rui Patricio, Abel (Romagnoli 46), Tonel, Anderson Polga, Grimi, Veloso, Bruno Pereirinha, Joao Moutinho, Izmailov (Gladstone 85), Vukcevic, Tiui (Adrien Silva 79). Subs Not Used: Stojkovic, Silva, Purovic, Farnerud.
Goals: Vukcevic 69.
Ref: Alon Yefet (Israel).
BBC Sport Player Rater man of the match: Bolton's Gavin McCann 7.70 (on 90 minutes).
• Please note that you can still give the players marks out of 10 on BBC Sport's Player Rater after the match has finished.
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