Raheem Sterling scored his first Arsenal goal and Jack Porter became the club’s youngest ever starter in a 5-1 rout of Bolton in the League Cup on Wednesday, while Liverpool reached the last 16 with a 5-1 win against troubled West Ham.

Sterling marked his maiden Arsenal start following his transfer deadline day move from Chelsea with a second-half strike in the third-round tie at the Emirates Stadium.

The 29-year-old will hope his goal marks the start of a career revival after a disappointing two-year spell at Chelsea.

“He was great. He’s started to show glimpses of what he can do. Physically, he needs to get to the level we require, but it was a massive step today,” Gunners boss Mikel Arteta said.

Arteta had made seven changes from Sunday’s stormy 2-2 draw at Premier League champions Manchester City, including giving goalkeeper Porter his record-breaking debut in place of the injured David Raya.

Aged 16 years and 72 days old, Porter was the youngest player ever to start for Arsenal, surpassing the previous record holder Cesc Fabregas, who was 16 years and 177 days when he played against Rotherham in 2003.

Porter was Arsenal’s second youngest ever player overall after Ethan Nwaneri, who was 15 years and 181 days, when he made his debut in 2022.

“Jack has been training with us since pre-season. He reacted really well and was really composed. What an experience,” Arteta said.

Arsenal will travel to Championship side Preston in the last 16, with the tie of the fourth round pitting Tottenham against Manchester City.

Liverpool’s bid to retain the trophy will continue at Brighton, while Manchester United face Leicester.

AFC Wimbledon or Newcastle, whose tie was rearranged due to flooding at the League Two side’s stadium, will host Chelsea.

Declan Rice put Arsenal ahead after 16 minutes with a clinical finish from the edge of the area for his first goal this season.

Nwaneri, 17, doubled Arsenal’s lead in the 37th minute with his first goal for the club and struck again from 12 yards four minutes after half-time.

Porter had to pick the ball out of the net in the 53rd minute when Aaron Collins jinked around him and slotted home.

Sterling netted in the 64th minute, tapping in after Saka’s cross was spilled by Bolton keeper Luke Southwood, and Kai Havertz grabbed the fifth from close range in the 78th minute.

West Ham in turmoil

At Anfield, Diogo Jota and Cody Gakpo scored twice as Liverpool’s understudies demolished West Ham to increase the scrutiny on Julen Lopetegui.

Under pressure after winning only one of his first five league games since replacing David Moyes, Lopetegui made eight changes from the 3-0 defeat against Chelsea last weekend.

That loss had made Lopetegui the first West Ham manager to suffer three consecutive defeats at home to start a season.

The Hammers took a surprise lead in the 21st minute as Kostas Tsimikas’s miscued clearance deflected in off Liverpool defender Jarell Quansah for a farcical own goal.

And Jota equalised four minutes later, the Portugal forward out-jumping West Ham keeper Lukasz Fabianski to nod in Federico Chiesa’s volley.

Jota struck again in the 49th minute as he exchanged passes with Curtis Jones and drilled past Fabianski.

Mohamed Salah came off the bench to score in the 74th minute with a simple finish after Alexis Mac Allister’s shot was pushed into his path.

West Ham were in disarray and Edson Alvarez was sent off in the 76th minute for a second booking after chopping down Salah.

Capping another torrid day for Lopetegui, Gakpo smashed home from 18 yards in the 90th minute and then guided a deflected effort beyond Fabianski moments later.

“We don’t deserve this score because we did a lot of good things. They scored an offside goal. I’m sorry for our fans,” Lopetegui said.

Liverpool boss Arne Slot added: “Since I’ve been here it’s never been easy, although sometimes the result looks different.”