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The difference between the Tube and the DLR is that whilst the Underground serves most of Greater London, the DLR only serves the Docklands area in the east. Another difference between the two is that the trains of the Underground are manually controlled with a driver, whilst the DLR trains are fully computer controlled. It's actually incredibly clever.
As you can see from the Tube map, not all trains will going to Lewisham, which is the branch you need if you want to get off at Cutty Sark. For this reason, you may need to change at either Poplar or Canary Wharf.
Now, tickets. Oyster and paper tickets are all accepted on the DLR, just as they are on the London Underground. The advantage of an Oyster card is that it's interchangeable with most forms of transport across the capital. Tube, DLR, Buses and Trams all accept Oyster. As always, you must remember to touch in and touch out at every stop to avoid paying a penalty fare. And a handy tip; although all Tube stations seem to have ticket barriers, quite a few DLR station's dont (Cutty Sark doesn't for example). Just because there aren't any barriers doesnt mean you don't need to touch out. Make sure you always find the touch pad when leaving the station.
So in answer to your question, no, you will not need to pay more. Just make sure there's enough money loaded onto your Oyster PAYG account. If your not sure of how much is on there, go to any ticket machine on the Tube or DLR and swipe the card. Then you can see your balance and topup if need be.
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