Rafael van der Vaart had given Spurs the lead with a free-kick, but Happy Jele’s super strike earned Bucs a share of the spoils.
But for the last five minutes, Spurs were all over Pirates in the first half, with Gareth Bale the main destroyer down the left flank.
It was the Welshman who came closest to opening the scoring in the first half – getting past two challenges before firing a volley over the bar.
Bucs were keeping possession, but hardly penetrating and resorted to long-range shots from Daine Klate and Isaac Chansa which failed to test Brad Friedel.
Spurs took a deserved lead on 17 minutes – Rafael van der Vaart curling a sublime free-kick into the corner after Ruben Cloete had fouled David Bentley.
Bongani Ndulula came close with a near-post header from Jele’s cross, before Bale again weaved his magic – surging down the left and putting in a cross which just eluded Jermain Defoe.
Bale forced Meyiwa into a smart save from a free-kick before Pirates equalised somewhat against the run of play on 40 minutes – his thunderbolt from the right of the area catching Friedel by surprise and flying into the top corner.
With their tails up, Bucs went in search of another goal and almost found it a few times – Segolela shooting straight at the goalie; Ndulula’s flicked header going just wide; and Daine Klate’s finish being ruled out for offside on the stroke of half-time.
Predictably, there were a spate of changes at the break, but Bale was still on nearly gave Spurs the lead again – his surging run down the left finding Aaron Lennon unmarked in the area, but the Englishman’s strike was poor.
Spurs came even closer on the hour-mark as Robbie Keane played in Niko Kranjcar, who cleverly chipped the advancing Senzo Meyiwa, but debutant Siyabonga Sangweni was back to clear off the line.
But like in the first half, Pirates finished the stronger of the two sides. Substitute Mark Mayambela flashed a shot wide, and it took an excellent last-ditch tackle from Michael Dawson to prevent Oupa Manyisa from scoring with 10 minutes to go.
Bucs turned on the skills and tricks in the last few minutes, but could not find that elusive winning goal.
Orlando Pirates: Senzo Meyiwa, Happy Jele (Njabulo Ntusi 63’), Lucky Lekgwathi (Robyn Johannes 63’), Rooi Mahamutsa (Siyabonga Sangweni 46’), Reuben Cloete, Andile Jali (Clifford Ngobeni 63’), Oupa Manyisa, Isaac Chansa (Mark Mayambela 46’), Tlou Segolela (Rudolf Bester 78’), Bongane Ndulula (Ndumiso Mabena 75’), Daine Klate (Sameehg Doutie 46’)
Tottenham: Brad Friedel, Kyle Naughton (Kyle Walker 46’), Younes Kaboul (Michael Dawson 46’), Bongani Khumalo, Danny Rose, David Bentley (Aaron Lennon 46’), Luka Modric (Niko Kranjcar 58’), Wilson Palacios (Vedran Corluka 46’), Gareth Bale (Jermaine Jenas 58’), Rafael van der Vaart (Robbie Keane 46’), Jermain Defoe (Roman Pavlyuchenko 46’)