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Migori Youth and Mombasa United meet at Awendo Green Stadium on Sunday, with both newly promoted sides seeking their first FKF Premier League victories of the season.
The teams enter the fifth round in contrasting positions despite sharing the same immediate objective.
Migori have collected three points from three matches and remain unbeaten, while Mombasa have managed just one point from four games and occupy the bottom position.
Migori's opening results suggest a team capable of competing in the top flight, but they have yet to turn that promise into maximum points.
Draws against Kenya Police, Mathare United and Shabana have left Salim Babu's side waiting for their first win.
Their latest outing ended in a 1-1 draw against Shabana, where Migori recovered to earn a point.
They will now hope that playing at Awendo Green Stadium provides the opportunity to take a further step forward.
Mombasa United, by contrast, have found the transition more difficult.
They drew 0-0 with Kenya Police but subsequently lost to KCB, Mara Sugar and Kakamega Homeboyz.
Their latest defeat was a 3-1 loss to KCB, leaving the coastal side with only one point and a goal difference of -4.
Coach Abdulhamid Moallin will be looking for a stronger response as the team attempts to avoid allowing its difficult start to continue.
The difference between the clubs is reflected in the table.
Migori have conceded fewer goals and collected points more consistently, but they still need a victory to move away from the bottom half. Mombasa need an improvement in both results and defensive solidity.
The teams are familiar with one another from their National Super League days.
Migori won their home meeting 3-2 before the return fixture in Mombasa ended goalless.
Those encounters offer some context, but the circumstances have changed since both clubs gained promotion.
Today's meeting will test their ability to adapt to the demands of the top flight.