Cliftonville beat Warrenpoint Town 4-3 after extra-time in an incident-packed Irish Cup tie in which 14 players were booked and two sent off.
Defender Jamie Harney scored a hat-trick while Town manager Matthew Tipton was one of the players dismissed.
Premiership sides Linfield, Coleraine, Ballymena, Ards, Dungannon, Crusaders and Glenavon all went through.
Ballinamallard saw off Immaculata 4-2 in a fifth round which did not produce any surprise results.
Cliftonville, who last won the cup back in 1979, will be relieved to have made it into the last 16.
They went behind to an early goal by Martin Murray but responded to lead through Harney and Ross Lavery.
Warrenpoint, given hope when Reds defender Jamie McGovern was sent off for lifting his hands to Town striker Darren Murray, equalised through Murray’s second of the afternoon.
Town boss Tipton, who brought himself on late in the game, was sent-off for a high tackle in the last play of normal time.
The 10 men of Cliftonville went 4-2 up through two goals by unlikely hat-trick hero Harney with sub Darius Roohi pulling a late one back for Warrenpoint.
Premiership title challengers Coleraine romped to a 7-0 win over Lisburn Distillery with goals by Gareth McConaghie, Stephen Dooley, Jamie McGonigle, Martin Smith, Ian Parkhill and Matthew Kirk (2).
Linfield’s scorers in their 5-0 home triumph over Glebe Rangers were Kirk Millar (2), Mark Haughey, Josh Robinson and Matthew Clarke.
Jordan Forsythe scored after just 70 seconds for Crusaders against Maiden City but the intermediate side kept the Premiership leaders at bay until David Cushley made it 2-0 near the end.
Matthew Shevlin netted twice and Kyle Owens and Tony Kane got the others as Ballymena won 4-0 against Moyola Park.
Ryan Curran scored two as Ballinamallard, bottom of the Premiership with just one win all season, battled to a 4-2 victory over Immaculata.
Stewart Nixon also netted a double as Ballyclare Comrades beat Portadown 2-1 after extra time at Shamrock Park where each side had a man dismissed.
Extra-time was also required at Carrick where Glenavon, cup winners in 2014 and 2016, emerged 3-1 winners.
Bobby Burns, James Singleton and Andrew Mitchell scored for Glenavon while Mark Surgenor netted a penalty for Rangers before being sent off in extra-time.
Curtis Allen and a Brian Toland own goal proved enough to give Glentoran a 2-1 win away to Lurgan Celtic.
Dungannon Swifts eased into the sixth round by beating Limavady United 4-0 – Ryan Harpur (2), Kris Lowe and Jonny Lafferty on target at Stangmore.
|Tennent’s Irish Cup fifth round – Saturday 6 January|
|Ballymena Utd||4-0||Moyola Park|
|Carrick Rangers||1-3 aet||Glenavon|
|Cliftonville||4-3 aet||Warrenpoint Town|
|Dungannon Swifts||4-0||Limavady Utd|
|Newry City||2-0||H&W Welders|
|Portadown||1-2 aet||Ballyclare Comrades|