This is a list of all transfers that the top tier Macedonian league clubs made during this winter transfer window.

Most of the clubs were rather quiet, with the leader Vardar being inactive on the market due to the 12 months transfer ban that they were given by UEFA in the summer. From the other clubs, the most active seemed to be Rabotnichki, Shkendija and Shkupi who made some drastic changes in their squads, while the remaining clubs mostly made small changes from the first half of the season.

The winter transfer window in Macedonia started on 15 January and ended on 12 February.

The list will be constantly updated as free agents can still be signed by any of the clubs.

Last update: 11 March 2020

Vardar
IN: /
OUT: Nikola Serafimov (Vysočina ), Stefan Naumcheski (loan – Tikvesh)

Shkendija
IN: Ardin Dallku (Vorskla ), Valon Ahmedi (Inter ), Aldair Sapalo Amaro Neto (Bangor City ), Ján Krivák (Karviná ), Aboubaker Es Sahhal (Guingamp ), Florent Ramadani (loan end – Drita), Bashkim Ljama (loan end – Korabi), Lek Luma (loan end – Vardari)
OUT: Egzon Bejtulai (Helsingborg ), Zeni Husmani (Domžale ), Shefit Shefiti (Renova), Jakup Berisha, Ramin Alii (Shkupi), Saladin Mustafi (retired), Ensar Ljuma, Besart Redjepi (loan – Gostivar), Stênio Marcos da Fonseca Salazar Júnior (Riga ), Berat Beqiri (Triglav ), Agan Zuber (Drita), Bashkim Ljama (Chaklani), Almir Redjepi (loan – Vlazrimi 77), Lek Luma (loan – Drita)

Akademija Pandev
IN: Angel Granchov (Flamurtari ), Bojan Najdenov (no club), Milan Basrak (Smederevo ), Ndue Mujeci (Cihangir ), Mite Cikarski (Gaz Metan )
OUT: Marko Rajković (Happy Valley ), Mario Maslać (Radnički ), David Denkovski (loan – Kit-Go), Gligor Donchev (loan – Osogovo), Vasko Kocev, David Stojkov (loan – Belasica), David Atanaskoski (Makedonija GjP), Mihail Manevski (Bregalnica), Mario Krstovski (loan – Rabotnichki)

Sileks
IN: Burhan Mustafov (Struga), Nenad Marinković (Mačva ), Filip Osman (Kolubara ), Darijo Trajanovski (loan end – Plachkovica), Antonio Bozhinoski (Madjari Solidarnost), Filip Kostovski (Nju Stars)
OUT: Andreja Efremov (Vllaznia ), Stefan Kocev (Enosis Aspropyrgos ), Andrian Chavoli (Strumska Slava ), Darko Dodev (Bregalnica), Filip Duranski (Sereď ), Darijo Trajanovski (loan – Osogovo), Denis Ristov (?)

Makedonija GjP
IN: Martin Kovachev (Dunav ), Filip Petrov (Borec), David Atanaskoski (Akademija Pandev), Tome Kitanovski (Kukësi )
OUT: Blagoja Spirkoski (Pelister), Benjamin Demir, Bianor das Graças Lima da Silva Neto (Shkupi), Alban Sulejmani (Struga), Hristijan Pecov (Rabotnichki), Luka Trajkoski (Tikvesh), Jovica Radevski (Kadino)

Struga
IN: Fjoralb Deliaj (Flamurtari ), Sedat Berisha (Drita ), Alban Sulejmani (Makedonija GjP), Angelo Demaj (Shkëndija ), Dardan Miftari (no club)
OUT: Hristijan Dragarski (Pelister), Aleksandar Dalcheski (Labunishta), Burhan Mustafov (Sileks), Agon Hajredini (loan – Drita), Bledar Istrefi (Veleshta)

Shkupi
IN: Jakup Berisha, Ramin Alii (Shkendija), Benjamin Demir, Bianor das Graças Lima da Silva Neto (Makedonija GjP), Filip Lazarevski (Labunishta), Darko Glishikj (Arda ), Canberk Yurdakul (loan – Bursaspor ), Faouly Keita (Ndiambour ), Ezeora Ebere Ogadi (Oyah Sports )
OUT: Mevlan Adili (Vllaznia ), Alban Miftari (Vardari), Enes Azizi (?), Marin Jurina, Nermin Hajdarević (loan end – Čelik ), Bojan Gjorgievski (Kit-Go), Filip Stojanovski (Ferizaj ), Musli Ljika, Djemail Esati (loan – Gostivar), Besir Ramadani (Gostivar), Thulio Cler de Freitas (Serranense ), Basilio Ndong Owono Nchama (Westerlo ), Hamza Ramani (Vlazrimi 77), Abdulkadir Zango (?), Onyebuchi Emmanuel Ifeanyi (?)

Borec
IN: Dario Desnikj (Kadino), Nikola Radović (Bačka ), Aleksandar Anastasov (Neuhof 1910 ), Nikola Risteski (Kit-Go), Fernando Silva dos Santos (CA Juventus ), Darko Jocikj (Osogovo)
OUT: Simeon Hristov (Vllaznia ), Filip Petrov (Makedonija GjP), Stefan Bogdanovski (?), Vladimir Zhoglev (Skopje), Đorđe Ivljanin (Pajde ), Jovan Velev (?), Oliver Peev (Kalamata, Greece), Filip Ristovski (?), Martin Blazhevski (?), Matej Milenkov (Kadino)

Renova
IN: Djelil Abdula (Llapi ), Alush Gavazaj (Vushtrria ), Shefit Shefiti (Shkendija)
OUT: Ljavdrim Skenderi (Gostivar), Ilber Bekjiri (Korabi), Ardit Demiri (Drita)

Rabotnichki
IN: Branislav Trajković (no club), Din Alomerovikj (La Nucía ), Mario Krstovski (loan – Akademija Pandev), Hristijan Pecov (Makedonija GjP), Jordan Lomba Mpiandi (Waremme ), Yannick Dao (Santa Rosa ), Hristijan Veceski, David Bopkov (Pobeda), Draško Đorđević (Sinđelić ), Milosh Tosheski (Zemun ), Mario Stankovski (loan end – Gostivar), Sumer Hasan (loan end – Vardari)
OUT: Ivan Marković (?), Alexander Borja Córdoba, Ljavdrim Fazliu (Pelister), Kristijan Ackovski (Bregalnica), Mario Stankovski (loan – Sasa), Meldin Jusufi (Radnik ), Filip Stojchevski (Sioni ), Strahinja Krstevski (loan end – Crvena Zvezda ), Yaggo Vitorino Silva Gomes (Os Armacenenses ), Nemanja Ilić (Samutsongkhram ), Marko Klisura (?), Boško Papović (Hajduk ), Oliver Dishlievski (Skopje), Sumer Hasan (loan – Labunishta), Leonid Redev Jankulovski, David Spasovski, Nikola Andreski, Marko Andonovski (Kadino)