Sayid and Tom are two characters who have not had very much narrative interaction, but as soldiers in their respective armies, have had a few skirmishes, with Sayid on the losing side two times out of three (and that last one was only a win because of things that Sayid wasn't responsible for). Which is not to say that I'm totally bashing Sayid or anything; he is all kinds of teh awesome. Going back to the tactics thing, he is the baddest bad ass on the Island in personal combat. I will never write up an entry for "Jason & Sayid", so let's just that out of the way: breaking a guy's neck with your calves, while bound and gagged, no less, is a TOTAL win.
The first Sayid/Tom encounter is not direct, but it is interesting. In season 2, Sayid comes up with a plan to lure the Others into a trap by the Pala Ferry. Except Tom and the Others are just a tad more clever, and instead use the Galaga submarine (we think) to approach Desmond's sailboat by sea, and they engage Sun, with Colleen ending up shot in the gut. So, Sayid's strategy proved to be completely outwitted, and they ended up without a sailboat.
The next time Sayid and Tom had interaction was in season 3, when Sayid, Locke, Kate and Rousseau infiltrated the Barracks. First, hiding in the bushes, Sayid and crew were excited to see Jack running towards them, only to figure out that he was playing touch football with Tom, who notably threw like a girl. Their sneaking doesn't work for long, however, as Kate goes to talk to Jack, and she and Sayid are promptly captured by the Others' crack kidnapping crew. There is not a ton of Sayid/Tom direct interaction during all this, but it applies in as much as Sayid and Tom are sort of the "military" leaders of their respective groups, and once again, the Others have the upper hand. Sayid remains tied up to a swing set until Juliet and Kate come back for him and Jack in Left Behind.
Finally, the last interaction between Sayid and Tom is their biggest, as Sayid leads a trio of Losties (Bernard and Jin) in an attempt in the season 3 finale to blow up a large team of Others who are expected to be invading the beach camp. Bernard and Sayid both hit their targets, but Jin's pistol doesn't have the same sort of aim, and so a few surviving Others, led by Tom, are able to gain the upper hand. So, yet another Sayid plan goes badly. The Others hold our three Losties hostage (again for Sayid), and there is some sort of mind game where Ben tells Tom to kill them, but he doesn't actually do it (we don't know for sure why that is). And then Hurley comes crashing through in the DHARMA van, killing Ryan, and allowing Sayid to get all kick ass with the killing with your feet thing, and Sawyer kills Tom. Another example of a strategic plan going wrong, but Sayid's tactical skills shine.
In conclusion, Sayid is an amazing soldier, but not a masterful general. Tom, on the other hand, seems very good at planning attacks, but we never really see any evidence that he is much of a fighter. With Tom dead, and Sayid in the future now, it's unlikely we will ever see them encounter each other again, unless it's some sort of ghost/vision thing.