The Railway Skirmish is an event on August 22, 2020, in which a small conflict broke out between Tommy and Dream after Tommy accidentally hit Dream with a minecart and stole his belongings. Tommy and Tubbo originally planned to collect his things and give them back, but they realised this was their way to gain leverage over him and quickly ran off with his items.

Tommy wanted to trade Dream his items for his valuable discs that he lost, but Dream refused the offer, stating that he had no emotional attachment to his items and could easily grind them out again stronger than ever. Dream offered to trade Tommy his dead horse Spirit's leather for his items, but Tommy refused. Because of this, Dream killed Tommy's horse while he was tabbed out.

Eventually, Dream and Tommy traded, with Tommy now having Spirit's leather and Dream having all of his items except for his maxed Netherite Sword. After this, Tommy tried to convince Skeppy to give him one of the discs for Spirit's leather, but Skeppy didn't accept the trade.

Still thinking he could get his discs back, Tommy teamed up with Sapnap to try and kill Dream after chasing him around thinking he had the disc on him. Sapnap then killed Dream and took most of his stuff with the disc not being there. Tommy picked up Dream's pickaxe, and Sapnap quickly betrayed Tommy under the stress of threats from Dream by killing him.

Even though it seemed most likely that the sword had despawned and was gone for good, Tubbo led Tommy to an undisclosed location and told him to open the chest there. Tommy did so, and low and behold, there was Dream's sword, tucked away in L'Manberg's possession. They now possessed two pieces of leverage over Dream; his sword, and Spirit's leather.