Cristiano Ronaldo scored his 700th career goal as Portugal fell to a 2-1 defeat to Ukraine, who became the fifth team to qualify for Euro 2020.
Roman Yaremchuk gave the home side an early lead before West Ham’s Andriy Yarmolenko added a second before the half-hour mark.
In the second half, Portugal were awarded a penalty and Ronaldo stepped up to take it, reaching the milestone with a drive into the top right corner.
The Portugese forward scored his first goal almost exactly 17 years ago and became the sixth player in history to reach 700 goals.
The result leaves Portugal and Serbia to contend for the second qualifying spot.
England thrashed Bulgaria 6-0 in Sofia during a game which was halted twice for racist abuse directed against some Three Lions players.
The visitors bounced back from Friday’s surprise defeat to the Czech Republic to move closer to qualification for Euro 2020.
Marcus Rashford and Harry Kane scored and Ross Barkley and Raheem Sterling each bagged a brace.
France let an advantage slip as they were held to a 1-1 draw at home to Turkey.
The hosts had to wait until the 76th minute to break the deadlock, with Olivier Giroud coming on just four minutes before he headed home.
The lead lasted only five minutes before Kaan Ayhan nodded the ball into the back of the net to level, as the two sides remain tied on 19 points at the top of Group H.
Elsewhere in Group H, Iceland returned to winning ways after back-to-back defeats with a 2-0 win over Andorra, while Albania stormed to a 4-0 victory in Moldova.
In Group B, Fulham’s Aleksandar Mitrovic scored twice as Serbia kept their qualification hopes alive with a 2-1 win in Lithuania, while in Group A, Kosovo beat Montenegro 2-0.