I am starting to get a better picture of the start of the Battle of Portland. The Dutch approached from the northwest. Apparently, west to east, the Dutch were De Ruyter, Florissen, Tromp, and Jan Evertsen, and their squadrons. Directly south of Tromp was Lawson with about a dozen ships. To the immediate west of Lawson was Blake and Deane, along with about a half-dozen ships. To the west of them was Penn and another dozen ships. Altogether, there were only 30 English ships, at the point of collision. The rest, including Monck and his squadron, were to the leeward.
Tromp headed for Blake, but was repulsed by a circle of ships protecting Blake, in the Triumph. During the fight, however, Blake was wounded by a bar shot. He never healed between and when he died in 1657.
Penn was in bigger trouble. De Ruyter's squadron sank the Dutch prize, the Sampson (26 guns) and took the Prosperous, Assistance, and Oak. De Ruyter had personally taken the Prosperous (42 guns).
Penn was rescued by the arrival of Lawson. Jan Evertsen had taken his squadron against Lawson, and was decimated. When Lawson arrived, he broke the Dutch attack on Blake and retook Penn's ships that had been captured.
The Dutch were forced to retreat to protect their merchant convoy from Lawson's frigates. That ended the first day of the Battle of Portland.
The Dutch had started in a very favorable position, and had actually taken one flagship, the Assistance, that of John Bourne, Rear-Admiral of the Blue. Penn and the Generals were hard pressed, and with a little luck, the Dutch could have taken them, as well, as the Dutch had about 80 warships to the 30 English ships, as first contact.