Leaders Makedonija GjP defeated Vardar and will stay on the top with seven points lead in front of Milano who were defeated away to Pelister in the last round of the 2008/09 season before the winter break. The season will continue in March, 2009.
Vardar Skopje – Makedonija GjP 0:1 (0:0)
83' De Brito(pen)
There's no end for Vardar's agony. 11 matches without a win (9 in the league and 2 in the cup), players are being beaten by the fans, the president Kostovski resigns from the club… With the current situation in the club, everybody has been hardly waiting for the winter break.
The derby of the round in which Vardar hosted leaders Makedonija was played in beautiful atmosphere created by both supporters groups, but sadly there were no more then 1000 fans who came to see the match on the cold weather on Gradski in Skopje. The attack over Vardar's players gave them a small motivational boost, but their fighting spirit lasted only in the opening minutes. After the leveled play, Vardar had the first big chance in the 17th minute when Ejupi from the right side assisted Polozani in the box who shot just next to the goal. Few minutes later, Vardar's defenders failed to mark the veteran Milevski who sent a header, but it missed the target. In the 35th minute after a corner kick from the right side, the excellent 16-years-old Vardar defender shot on Makedonija's goal, but the goalkeeper Pavlovic saved his goal. Towards the end of the first half, Vardar had another threat on the goal when Milisavljevic took a free kick from 25meters, but it gave no serious trouble for Bojan Pavlovic.
The beginning of the second half brought no excitements. Both teams struggled to create some serious chance and the play was mostly on the middle of the bad pitch. The first real excitements came in the last 10 minutes. After a fast counter attack, De Brito came out alone against Pacovski who saved his shot. But only a minute later, the same chance was repeated, but this time the Brazilian tried to dribble the goalkeeper who fouled him in the box and the referee whistled for a penalty kick. The current leading league striker De Brito decided to take the kick and scored his 10th goal. Few minutes later, the other Brazilian Washington had the chance to confirm the victory but failed to score from close range. In the last minutes of the match, young Mirko Ivanovski was sent off, but it didn't caused trouble for Makedonija to hold the lead in the last seconds.
With this win, Makedonija will spend the winter break on the leading position with 37 points, while Vardar will have though period for consolidation of the club after the sponsor, the board and the coach have announced their resignation.
Pelister Bitola – Milano Kumanovo 2:0 (2:0)
34' Dimitrovski, 45' Simonovski
After eight matches without a win, Pelister's players entered this match with huge motivation for winning points and escaping the bottom of the table before the winter break. Second placed Milano arrived in Bitola as favorites against last placed Pelister, but after the disappointing performance, they left home with their heads down.
Pelister had a small domination on the pitch, but the first real chance came in the 26th minute when Presilski sent a long pass to Dimitrovski in the box who shot from the left side, but his shot went close to the goal. After a fast tempo, and interesting match, Pelister came in the lead and finally scored after 588 minutes without a goal. Glavevski sent a cross and Dragan Dimitrovski scored a fantastic goal with his heel. In the last seconds of the first half Simonovski took a corner kick and the defender Ljupco Micevski doubled the lead for Pelister with a nice header.
Milano's disappointed coach Bilbil Sokoli made a surprising move and used all three substitutions on the half time. Those changes could have given an effect in the 52nd minute when Ristov hit the bar of Pelister's goal. But Milano's pressure didn't last for long as Pelister managed to controll the play and keep the lead. The most serious chance came towards the end of the match when Glavevski came out alone with the goalkeeper but failed to score.
With this win, Pelister's players showed that their place is not in the relegation zone and with few changes in the winter break they can achieve a lot higher placements.
Pobeda Prilep – Rabotnicki Skopje 0:0 (0:0)
Pobeda and Rabotnicki started a fast match, but the play was mostly on the middle of the pitch as the defenders successfully stopped the attacks on both sides. The few hundreds fans on "Goce Delcev" stadium in Prilep saw interesting match with attacking football and few good chances. Kirovski from a free kick for Rabotnicki and Aceski twice for Pobeda had the most serious chances in the first half.
Right on the start of the second half, Savic had good opportunity to score, but his shot from close range went over the goal. Rabotnicki had a small domination in the second half with few shots on goal, but Pobeda's goalkeeper and defenders saved their goal. Later in the second half, the players didn't show much as the nervous grew and there was a lot of stoppage time. After the few situations, the referee Mantev sent Pobeda's sports director Marjan Stojkoski – Manta off the pitch.
After the 90 minutes of interesting and leved match without goals, Pobeda and Rabotnicki shared the points.
Sileks Kratovo – Metalurg Skopje 2:2 (1:0)
15' Markovski, 69' Andonov – 58' Popovski(pen), 77' Naumovski
Sileks and Metalurg played the highest scoring match in this round. Blagojce Markovski scored the opening goal in the 15th minute. Later in the first half Gligor Gligorov had another chance to double the lead for Sileks but he missed the opportunity.
In the 58th minute, Shalevski fouled Gjurcevski in the box and a penalty kick was awarded to Metalurg. Aleksandar Popovski took the penalty kick and equalized the score. Sileks came in the lead again in the 69th minute with the goal by Andonov, but few minutes later, Naumovski scored and equalizer which was the last goal in the match. In the last minutes of the match, after a small brawl between the players, Dzangarovski was sent off and Sileks played the last minutes with 10 men on the pitch.
Renova Dzepciste – Napredok Kratovo 1:0 (1:0)