Two men, each about 5-feet-8 to 6 feet tall, pointed guns at the victims and struck one of them in the face two to three times, causing him to fall to the ground, police said.

The first robbery was reported in Brookline about 2:15 a.m., Brookline police said. The two victims were skateboarding in the area of St. Paul and Dummer streets when they were approached by a dark-colored sedan, one victim told police.

Police are investigating whether there are any connections between five armed robberies that occurred over about a 45-minute period in neighboring areas of Brookline, Boston, and Cambridge early Friday.


The suspects took a cellphone, a black wallet with a Rockland Trust debit and credit card, a black backpack with a City Year logo, and keys. They fled in the sedan and headed toward Beacon Street, police said. The wallet and backpack were later found on the street.

One of the victims reported that the suspects’ faces were covered, one with a red bandanna and the other with a black bandanna.

The victims took a taxi to Beth Israel Deaconess Medical Center, where police arrived at about 2:55 a.m. to speak to them.

The next two robberies were reported in Boston at 2:18 a.m. in an alley at 401 Beacon St., and at 2:34 a.m. near Highgate Street and Farrington Avenue in Allston, said police spokesman Stephen McNulty.

In both cases, a van drove past the victims and then stopped, at which point two males left the vehicle and pointed guns at the victims. Both victims were struck on the head once and robbed.

The Boston robberies “seemed to have similar modus operandi, but we are still investigating a possible connection,” McNulty said.

In Cambridge, police said two roommates were robbed at gunpoint while walking to their Putnam Avenue residence about 2:30 a.m. A vehicle, described by the victims as a dark-colored sedan, drove in the wrong direction on Franklin Street and then stopped.


Two males jumped out, stole the victims’ purses and a cellphone, and then drove away with a third suspect at the wheel, police said.

Another robbery was reported by a student to Harvard University police about 3 a.m., Cambridge police said. The student said he was robbed at gunpoint as he walked down Arrow Street toward Bow Street.

Felicia Gans can be reached at felicia.gans@globe.com. Follow her on Twitter @FeliciaGans. Sarah Roberts can be reached at sarah.roberts@globe.com. Follow her on Twitter at @heysarahroberts.