An interesting comparison on the effect of a 744 winglet versus a 777-300ER raked wingtip.
If departing with one winglet missing on the 744, the CDL has a weight penalty of approximately 9500 kg.
If departing with a raked wingtip missing on the 777, the penalty is a little over 11,000 kg(or more than 26,000 kg above 2000') but there is a MTOW restriction of over 50,000 kg. Plus other penalties such as reduced MQTW, a max altitude decrease, slightly higher V-speeds, and a reduction in CG envelope.