LONDON, Jan 28 (Reuters) - Holders Paris St Germain and Real Madrid both failed to seal automatic spots in the Champions League knockout round as they slipped out of the top eight on a frenetic final night of group-stage action across Europe on Wednesday.

Real Madrid missed out on direct qualification for the Champions League last 16 after Benfica goalkeeper Anatoliy Trubin scored in stoppage time to send his side into the play-offs, with Sporting also netting a late goal to help deny the record winners.

Goalkeeper Anatoliy Trubin scored a remarkable stoppage-time goal to claim a 4-2 win for Benfica against Real Madrid — sending Jose Mourinho’s side through to the play-offs as they condemned his former side to that additional knockout stage.

Real Madrid shockingly dropped into the Champions League knockout playoffs after a 4-2 defeat at Benfica, finishing ninth. Kylian Mbappé's brace wasn't enough as Benfica secured a playoff spot with a dramatic late header.

Angel Di Maria Former teammate of Kylian Mbappé at PSG, Angel Di Maria recently raved about the Real Madrid striker.Having played for both Real Madrid and PSG, Angel Di Maria is

The knockout phase of the Champions League will take place without Italian champions Napoli. Paris Saint-Germain and Real Madrid still slip out of the top 8.

Liverpool, Tottenham Hotspur, Barcelona, Chelsea, Sporting Lisbon, and Manchester City rounded out the teams to progress directly to the last 16. Reigning European champions Paris Saint-Germain and 15-time winners Real Madrid must now proceed to the knockout playoffs after finishing outside the top eight.

Arsenal defeated FC Kairat of Kazakhstan 3-2 at the Emirates Stadium on Wednesday night to stroll into the round of 16 of the UEFA Champions League (UCL) as group stage winners.

Real Madrid missed out on automatic qualification for the Champions League knockout rounds as they crumbled to a 4-2 defeat at Benfica on a frenetic final night of group-stage action across Europe on Wednesday.

LONDON — Real Madrid missed out on automatic qualification for the Champions League knockout rounds as they crumbled to a 4-2 defeat at Benfica on a frenetic final night of group-stage action across Europe on Wednesday.