Raila's ODM party's numbers in the National Assembly reduced from 85 to 83 in just one day, posing a major political headache for the opposition chief.
Raila is already battered following raids by President William Ruto that have seen a number of ODM lawmaker shift their allegiance to the ruling Kenya Kwanza alliance.
In the National Assembly, Ruto's United Democratic Alliance party has 137 members elected on the outfit's ticket.
Coming at a time when Raila is building momentum for his aggressive campaign against President Ruto's administration, the twin losses are a staggering blow to the opposition leader.
The Azimio leader could now have to juggle between firing up his Azimio rallies couched as public engagement barazas and dashing to ring-fence the two constituencies ahead of by-elections.
In Raila's strategic Kilifi stronghold, his key ally Harrison Kombe kissed the dust after the High Court in Malindi overturned his victory in the August 9 general election.
Kombe lost his Mgarini seat on Friday following a petition by UDA candidate in last year's general election Stanley Kenga.
The Malindi High Court ordered a by-election in Magarini, one of the seven constituencies in Kilifi county, citing massive irregularities in the election.
The High Court in Nairobi also nullified the election of ODM's Lagdera MP Abdikadir Hussein following a petition filed by UDA’s Abdiqani Zeitun.
Hussein, who ran on Raila's ODM party ticket, had received 5,939 votes to defeat Abdiqani Zeitun of the UDA party.
Mohamed Hire of Kanu came third with 3,277 votes.
The first runner-up, Abdiqani, filed a suit at the High Court, challenging Hussein’s victory, citing electoral malpractice.
The High Court ruled that there were elements of irregularities in the parliamentary election, and directed that a re-election be held on a date to be decided by the IEBC.
President Ruto and Raila are now bracing for a political showdown in Kilifi and Garissa following the fall of the two ODM lawmakers.
The speaker of the National Assembly Moses Wetang'ula will declare the seat vacant and a by-election held in 90 days.
This will happen if Kombe fails to move to the Court of Appeal or his petition flops.
In Garissa county, Ruto will be flexing muscles to parry away Raila from making in roads in the Northestern region.
Raila has not held any Azimio anti-government rally in the Northern Kenya with Ruto expected to rely on Defence Cabinet Secretary Aden Duale to capture the seat.
Duale successfully campaigned for UDA's Mohamed Dekow to succeed him in Garissa Township after he was appointed CS.
Dekow garnered 11,572 votes, beating his closest competitor Nassir Dolal Mohamed alias Jofle (UDM) who got 8,158 votes.
Stake will be higher in Magarini, Raila's perceived stronghold, with the mini—poll likely to escalate the political war between Ruto and Raila.
Ruto would be using the by-election to test his popularity in the region, especially after he picked former governor Amason Kingi as the Senate Speaker.
Kingi, the leader of the Pamoja African Alliance party, was Raila's key ally in the region when he served for two terms as Kilifi governor.
Kingi served as Magarini MP between 2007 and 2013 when he was elected the first governor of Kilifi county.
The by-election will also serve as a big test for Public Service Cabinet Secretary Aisha Jumwa.
She was appointed to the position after losing to ODM's Gideon Mung'aro in the Kilifi governor's race.
With the two top government officials, Ruto will be flexing his political muscles in the region through either the PAA party or his own United Democratic Alliance outfit.
On the other hand, Raila will be banking on Mung'aro to deliver the seat to ODM and also affirm his popularity as the de facto king of Coast politics.
However, lately Mung'aro had been warming up to Ruto, tipping ODM for a bruising political battle against the President's possible candidate in Magarini.
With Ruto and Raila expected to lock horns in Malindi, all eyes will be on former Mombasa governor Hassan Joho who has been missing in action in recent months.
Joho, Raila's deputy in ODM leadership, was a key cog of the Azimio campaigns in the last polls but appears to have stepped back as he has not attended the ongoing public barazas.
The mini-poll will come at a time when Raila has escalated his campaign against Ruto, whom he has accused of being in office illegitimately.
The opposition leader has called for mass action from next week insisting that President Ruto must vacate State House
