This morning, I wanted to experiment, using a difficult scenario for the Dutch, where they are outnumbered three-to-two, a the Battle of Plymouth. My plan, going in, was to maneuver as a group, not use a single line formation, and to keep wearing back and forth, always turning away from the wind. I upped the sails to "full sail", to get maximum effect. I also had the simulator speed close to the highest setting.
The key point is that I was aware of the Dutch position relative to the English, I kept the Dutch maneuvering along the edge of the English, and would focus on part of the battle, and would maneuver the entire group, based on part of the tactical situation. That allowed me to position the Dutch to "cross the T". You might think that you have to be in a single line to achieve that, but it is not the case. All you have to do is to be maneuvering as a group, and in a crossing situation.
This picture shows the Dutch crossing. There more pictures on AngloDutchWarBlog.com that show the crossing of the T, more vividly.