Both sides overcame tough opposition in the previous round to reach this stage, with Thursday's hosts getting past Galatasaray, while their visitors beat Trabzonspor in the quarter-finals.
Match preview
Istanbul Basaksehir began this year's Turkish Cup campaign in the fifth round with a home contest against Goztepe in December, and they punched their ticket to the round of 16 with a 3-1 victory before meeting Fatih Karagumruk with a quarter-final place on the line.
After that game was level at a goal apiece following regular time, their opponents looked set to come out on top in the extra 30 minutes, only for the Grey Owls to win a penalty in the 121st minute, which Deniz Turuc converted to force a penalty shootout, with Emre Belozoglu's side eventually coming out on top at that stage.
That booked them a difficult test away at fellow Istanbul giants Galatasaray in the final eight in early April, and they twice went ahead through Patryk Szysz and Danijel Aleksic, only for Kaan Ayhan and Mauro Icardi to draw their hosts level, before Szysz netted his second of the game in the 66th minute, deciding the tie as a result and sealing their semi-final place for the second time in their last three Turkish Cup campaigns.
Belozoglu's men now head into their latest cup tie on the back of somewhat of a rest, with their last outing being over a week ago when they beat Giresunspor 4-2 away from home courtesy of braces from Adnan Januzaj and Joao Figueiredo, before most recently seeing three points added to their tally at the weekend as they were scheduled to meet Hatayspor, who withdrew from the league early in the new year.
That result saw them maintain their position in fifth spot with 51 points on the board in the domestic top flight, and the Grey Owls will now turn their focus back to the Turkish Cup with the aim of taking a major step towards the final with a home victory to put them in the ascendancy on aggregate.
Their visitors will make the trip for their fifth outing of the cup campaign, having entered a round earlier than the hosts in a meeting with Amed Sportif in November, in which Ankaragucu dished out a 6-2 beating thanks to braces from Jese Rodriguez and Ghayas Zahid and goals from Sinan Osmanoglu and Anastasios Chatzigiovanis.
They would then meet Tuzlaspor and progress with a 2-0 victory as Rodriguez was again in the scoresheet alongside Federico Macheda, booking a tricky round-of-16 tie with giants Besiktas, in which they went ahead through Ali Sowe before Cenk Tosun forced a period of extra time with a 77th-minute equaliser for their visitors.
With the additional period not producing any more goals, the contest went all the way to a penalty shootout, and Ankaragucu would eventually prevail with no mistakes from the spot, before most recently meeting Trabzonspor in the quarter-finals under the new management of Tolunay Kafkas, and they would come from a goal down to eventually win 3-1 as Sowe netted a second-half brace alongside a goal from Lamine Diack.
Following that advancement to the final four, Kafkas's men will head into Thursday's trip in high spirits, having taken huge steps towards confirming their safety in the Turkish Super Lig since the triumph over Trabzonspor, adding 10 points to their tally in the last five scheduled matches, albeit with three of those coming from a cancelled meeting with Hatayspor.
Now on the back of a goalless draw at home to Kasimpasa last weekend, Ankaragucu will be keen to begin the cup tie with a positive result on their travels before welcoming Istanbul Basaksehir to the Eryaman Stadium for the second leg later this month.
Istanbul Basaksehir Turkish Cup form:
Istanbul Basaksehir form (all competitions):
D
W
D
L
L
W
Ankaragucu Turkish Cup form:
Ankaragucu form (all competitions):
L
L
W
L
W
D
Team News
Istanbul Basaksehir come into their cup tie with a bolstered squad compared to the one that was available for their last meeting with Giresunspor, as defenders Omer Ali Sahiner and Ahmed Touba and midfielders Lucas Biglia and Mahmut Tekdemir will all return to contention after serving suspensions.
Biglia and Tekdemir should come straight back into the engine room, allowing top scorer Danijel Aleksic to operate further forward as a result, while Touba will contend with Edgar Ie to join Leo Duarte in the middle of the back four.
Aleksic will support striker Joao Figueiredo, who opened his account for the club with a brace in the beating of Giresunspor, after arriving in February, while winger and fellow recent signing Adnan Januzaj is another danger man and also found the net twice in that game.
Ankaragucu centre-back Uros Radakovic has recently returned to contention after an injury layoff, but after their clean sheet last time out, Kafkas will likely stick with an unchanged back three of Kevin Malcuit, Atakan Cankaya and Nihad Mujakic on Thursday.
Their attack will be led by Ali Sowe, who has been a key man throughout the season thus far, netting 15 goals in 29 appearances across all competitions, including three in the last two Turkish Cup games.
He could again be flanked by Ghayas Zahid and Anastasios Chatzigiovannis, while Lamine Diack and Taylan Antalyali play key roles in midfield and will continue their partnership in the engine room.
Istanbul Basaksehir possible starting lineup:
Sengezer; Sahiner, Ie, Duarte, Erkin; Biglia, Tekdemir; Januzaj, Aleksic, Szysz; Figueiredo
Ankaragucu possible starting lineup:
Akkan; Malcuit, Cankaya, Mujakic; Kitsiou, Diack, Antalyali, Hanousek; Zahid, Sowe, Chatzigiovannis