Holders Tusker battle National Super League side Vihiga United at the Nyayo National Stadium on Sunday as the GOtv Shield tournament enters the business end.
Former champions AFC Leopards will also take on another second tier side Wazito at Nyayo Stadium on Sunday with the venue set to host all four quarterfinal matches this weekend.
It is the only trophy that Leopards have a realistic chance of lifting this season, leaving head coach Robert Matano under pressure to deliver the Cup they last won in 2013.
Since their 2-1 win over Bidco United in the last 16 of the competition three weeks ago, Leopards have suffered two losses and drawn once in the SportPesa Premier League.
Matano will be eager to guide his charges back to winning ways, with a semi-final slot up for grabs against Frank Ouna's Wazito.
With this being their maiden quarter-finals appearance in the competition, Ouna admits that his charges are massive underdogs going into the match.
"We can't compare ourselves to Leopards. They have good players, they have a lucrative sponsorship meaning that their players are more comfortable and more importantly, they have a coach who is experienced and who has won this particular cup before so it won't be easy for us," said Ouna.
SHARKS BATTLE ELDORET YOUTH
In Saturday's matches, Kariobangi Sharks face minnows Eldoret Youth hoping to continue with their fairytale run in the competition.
To get to this stage, Sharks stunned Sofapaka 3-1 in the last 16 at Nyayo, a result that makes them massive favourites going into this match.
"This is a team we don't know much about so already that is a challenge. It makes the game highly unpredictable so we have to be very cautious in our approach," Sharks coach William Muluya said.
Title holders Tusker will be without Noah Wafula (bereaved), Allan Wanga, Hashim Sempala, Martin Kizza and Moses Ndawula for their match against Vihiga United.
Vihiga, captained by former AFC Leopards playmaker Charles Okwemba, will be out to upset the stuttering brewers.
Bandari, winners in 2015, tackle Sony Sugar in the other quarter-final match up from 3.15pm on Saturday.
The winner of the tournament will walk away with a cash prize of Sh2 million and a ticket to represent Kenya in the Caf Confederation Cup next year.
Kariobangi Sharks v Eldoret Youth (Nyayo Stadium, 1pm)
Bandari v Sony Sugar (Nyayo Stadium, 3.15pm)
Vihiga United v Tusker (Nyayo Stadium, 1pm)
Wazito v AFC Leopards (Nyayo Stadium, 3.15pm)