Joining the sides in the inaugural edition of this competition is host nation Mauritius, who will take on Pakistan in their opening clash.
Match preview
Kenya fell to a 2-1 defeat against Iran when the sides' went head to head in an international friendly encounter at Azadi Stadium on March 28.
Engin Firat's men took the lead through Michael Olunga six minutes into the second period after which goals from Mohammad Mohebi and Ramin Rezaeian turned the game around.
That was a first involvement for the Harambee Stars in two years since they saw off the threat of Rwanda in their final 2022 World Cup qualifier.
Coming up next is the challenge of an opposing outfit who have been beaten in the each of the previous two editions of this fixture by a combined score of 7-1.
Currently on a run of just one victory from their last seven matches, Kenya will be keen to turn their fortunes around with a positive result here.
Djibouti were eliminated from the preliminary round of the Africa Cup of Nations qualifiers following a 1-0 defeat against South Sudan at St. Mary's Stadium-Kitende back in March.
Having suffered a 4-2 defeat in the first-leg, Mohamed Meraneh Hassan's men conceded a 54th-minute opener to Peter Chol which effectively put the tie beyond reach.
As a result, Riverains de la Mer Rouge have now lost nine straight games across all competitions since narrowly beating Somalia 1-0 in 2021.
More worryingly for the East Africans, they have failed to find the back of the net in five of the aforementioned nine outings heading into Monday's affair.
Kenya friendly form:
Djibouti friendly form:
Team News
Kenya's Michael Olunga is in good form having netted in each of his last four matches, making the forward one to keep a close watch on here.
Despite not featuring at club level since July, Aboud Omar retains his place in the squad and could be given the nod to feature right from the off.
Currently at the top of Djibouti's all-time scoring charts, Mahdi Houssein Mahabeh is a shock exclusion from his nation's 19-man squad for the trip to Mauritius.
With 19 international caps to his name, Innocent Mbonihankuye is set to become only the seventh player in history to reach 20 appearances for Djibouti
Kenya possible starting lineup:
Otieno; Omar, Ochieng, Otieno, Okumu; Akumu, Muguna, Odada; Olunga, Miheso, Abdallah
Djibouti possible starting lineup:
Mbonihankuye; Hamadou, Batio, Aden, Siad; Hassan, Mahabeh, Ahmed; Mohamed, Elabeh, Akinbinu